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Every business owner has a plan — or at least they think they do. They know where the important documents are stored, which child has expressed interest in the business, and what they want to happen if they retire, become disabled or pass away. The problem is that knowing isn’t the same thing as documenting, and when a crisis occurs, your family doesn’t get access to what’s in your head. They get access only to what’s in writing. 

I’ve talked with thousands of business owners and their advisors throughout my career, and one truth recurs: families rarely struggle because they lack love for one another. They struggle because they lack clarity. When a founder’s wishes are undocumented, spouses are left making impossible decisions. Children are left interpreting intentions. Advisors are forced to fill in gaps. At the very moment a family should focus on supporting one another, they are instead trying to answer questions that should have been resolved years earlier. 

The result is often confusion, conflict and damaged relationships. That’s why one of the greatest gifts a business owner can leave their family isn’t wealth — it’s clarity. A written legacy plan provides direction during moments of uncertainty and helps families move forward with confidence rather than guesswork. 

Half of owners will experience one of the 5Ds 

One of the biggest mistakes business owners make is assuming they have more time. They tell themselves they’ll create a plan after the next acquisition, after the next growth phase, or after they finally slow down. The reality is that life doesn’t always cooperate with those timelines. 

At the Exit Planning Institute® (EPI), we often talk about the 5Ds: Death, Disability, Divorce, Distress, and Disagreement. These events account for roughly half of all business exits and often arrive unexpectedly. They don’t care whether your succession plan is complete, whether your children are prepared, or whether you’ve had the difficult conversations. They simply arrive, forcing families to make major decisions under emotional and financial pressure. 

That’s why planning cannot wait until you’re approaching retirement. A legacy plan is not an end-of-career exercise. It’s a business and family responsibility that should begin now. When one of the 5Ds occurs, your family shouldn’t have to become detectives searching for clues about what you would have wanted. The answers should already exist in a written plan that reflects your values, intentions, and priorities. 

Start with values, not assets 

We have a warehouse that is a multi-use space, and it offers a helpful example of how legacy can be understood. 

In one area, we have a museum of sorts: memorabilia from generations of Snider family entrepreneurs. We’ve also documented 21 years of EPI. Additionally, we have a classic car collection that my son loves. 

Since I own a business with my dad and entrepreneurship is so central to my family’s history, from the outside, you might think that my children will simply inherit everything. But my son knows better. He knows that legacy must be earned. So, I made a deal with him.  

I told him that if he cleans that warehouse every time I think it needs cleaning, he’ll get the stuff inside it one day. Perhaps the lesson was too easily learned: the next week, without me asking, I found him in there during hour three of mopping the floors. 

He doesn’t take for granted that wealth is inherited. 

When families begin talking about legacy, they often start in the wrong place. The conversation immediately turns to ownership percentages, inheritance structures, and financial distributions. While those issues are important, they are not foundational. 

The first conversation should be about values. 

What does your family stand for? What principles guided the creation of your business and wealth? What responsibilities come with ownership? What kind of impact do you hope future generations will make? 

Families who establish clarity around values make better decisions when a crisis hits. They understand that wealth is not simply a resource to consume but a tool to create opportunity, strengthen relationships, and contribute to something larger than themselves. Wealth without context often creates entitlement. Wealth paired with values creates stewardship. 

This is why many successful family enterprises create written family values statements. These documents become a decision-making framework for future generations, helping them navigate opportunities and challenges long after the founder is gone. Markets will change, and circumstances will evolve. But clearly articulated values provide a compass that remains remarkably durable over time. 

Create a cadence of family conversations 

A single family meeting is not a family governance system. Yet many business owners treat communication as a one-time event rather than an ongoing process. 

The strongest family enterprises I’ve encountered establish a regular cadence of conversations long before ownership transitions become necessary. Some families gather quarterly. Others hold annual family meetings. The schedule itself matters less than the commitment to creating space for honest dialogue.  

These conversations shouldn’t focus exclusively on succession planning. They should explore family values, business performance, ownership responsibilities, philanthropic goals and long-term aspirations. Family members need opportunities to ask questions, voice concerns, and better understand both the opportunities and responsibilities associated with family wealth. 

Perhaps most importantly, these meetings help build trust. When communication occurs consistently over time, difficult decisions become easier because family members understand how those decisions are being made. Transparency creates confidence. Silence creates assumptions. And assumptions have a way of turning into conflict. 

I’ve often said that silence destroys more family wealth than taxes ever will. Families that communicate effectively don’t eliminate disagreement, but they create a framework for navigating it constructively. That may be one of the most valuable forms of legacy planning a family can undertake. 

A documented plan, in three areas 

At EPI, we recommend that business owners plan in three areas: personal, financial, and business. 

And even if there aren’t any children working in the business, a family should still have a window into all three of those areas. 

According to our research in the 2023 State of Owner Readiness Report, 39% of business owners plan to transfer the ownership of their business to their family. 

However, only 53% of families are aware of both the managerial and ownership transition plans. Worse yet, 27% of owners have fewer than one family meeting a year regarding the business, or none at all. 

That means a business built with the intention of selling to a third party or transitioning via an Employee Stock Ownership Plan may transition to family instead in a time of crisis. Or the opposite. Either way, a written plan, based on family conversations, is key. 

Here’s what must be included, at the very least: 

• Family Values and Legacy Statement: The principles that informed decision-making and the impact you hope your family will have. 

• Personal Financial Plan: Documented will, estate plan, and inheritance instructions, with account numbers and locations. 

• Business Transition Plan: How will the business transition, and why? Include a succession plan that accounts for whether each family member will experience ownership, leadership, or inheritance.  

These items should not be surprising to anyone in the family. Issues of fairness vs. equality should be worked out in advance and widely known. In addition, those plans should be revisited as family dynamics change, family members develop new skills and interests in the business, and wealth changes. 

Most families will have robust discussions during these planning sessions, if not outright disagreements. You may benefit from having an advisor lead these proceedings, acting as an independent third party that has the company’s and family’s best interests at heart. 

Every business owner has a plan — or at least they think they do. They know where the important documents are stored, which child has expressed interest in the business, and what they want to happen if they retire, become disabled or pass away. The problem is that knowing isn’t the same thing as documenting, and when a crisis occurs, your family doesn’t get access to what’s in your head. They get access only to what’s in writing. 

I’ve talked with thousands of business owners and their advisors throughout my career, and one truth recurs: families rarely struggle because they lack love for one another. They struggle because they lack clarity. When a founder’s wishes are undocumented, spouses are left making impossible decisions. Children are left interpreting intentions. Advisors are forced to fill in gaps. At the very moment a family should focus on supporting one another, they are instead trying to answer questions that should have been resolved years earlier. 

The result is often confusion, conflict and damaged relationships. That’s why one of the greatest gifts a business owner can leave their family isn’t wealth — it’s clarity. A written legacy plan provides direction during moments of uncertainty and helps families move forward with confidence rather than guesswork. 

Running a business while traveling sounds great in theory, but I’ve learned that it only works when you build the right systems around it.

Over the years, I’ve managed my businesses from different countries, sometimes while traveling with my family and sometimes while combining a trip with meetings or events.

Along the way, I’ve figured out what actually helps me stay productive without turning every vacation into another week at the office. Here are the strategies that work best for me.

1. Use AI agents to keep your business running

I’ve started using AI agents more actively in my businesses, and one of the biggest benefits I’ve noticed is how much easier they make it to step away from routine work. I can use them to organize information, monitor workflows, handle repetitive administrative tasks and deal with smaller processes that previously required someone’s constant attention. That becomes particularly valuable when I’m traveling, because I don’t want to open my laptop every hour just to check that everything is moving.

According to EverMind, most UK and Ireland C-suite leaders using AI agents report saving between three and 10 hours per week. For me, that’s the real value of AI agents: not replacing my involvement in the business, but reducing the number of small things that require it. When I only have a few hours to work during a trip, I’d rather spend them making decisions, talking to key people and solving problems that actually need me.

2. Create marketing content with AI while traveling

I’ve found that one of the harder things to maintain while traveling is a consistent flow of marketing content, particularly video. I don’t want every trip to involve filming equipment, long editing sessions or coordinating with a creative team just to keep my businesses visible online.

This is another area where I’ve started relying more on AI. I can take an idea, script or content I already have and use AI tools to turn it into something usable without being tied to my normal setup. According to PixVerse, 63% of video marketers have already used AI video tools to help create or edit marketing videos. I can use an AI video generator, for example, to experiment with social clips, promotional videos or different creative concepts directly from my laptop.

I still want the ideas and marketing strategy to come from me and my team, but AI makes the production side much more flexible — which is exactly what I need when I’m working from a hotel, airport or somewhere halfway around the world.

3. Use AI to improve and repurpose written content

The same approach works with written content. When I’m traveling, I rarely want to spend several hours staring at a blank document when I already have articles, posts and other material that can be turned into something new. I use AI to help me repurpose a longer article into LinkedIn posts, email content or shorter pieces, as well as to edit and improve drafts I’ve already written.

This is becoming a practical way for marketers to get more from the content they already have. According to WriterNinja, 39% of marketers using AI for content creation already use it to repurpose marketing content.

For me, AI solves another practical problem as well: English isn’t my native language. One of the easiest ways for me to create something while traveling is simply to press the microphone button in the AI assistant I’m using and talk through my thoughts as they come. Instead of worrying about perfect English or sentence structure, I can focus on the idea and let AI help me shape it into clear, polished writing afterward. It makes creating and repurposing content on the road much faster while still keeping the ideas and perspective genuinely mine.

4. Build a team that can handle hands-on work without you

One of the businesses I manage while traveling is surprisingly physical. I’ve built a network of microsites that generate leads for local construction services, from bathroom renovations and window installation to flooring, basement cleanouts and other hands-on jobs. When a lead comes in, my customer service team qualifies the customer and passes the job down to the local construction crews I work with, so I can focus on lead generation, marketing and managing the operation from wherever I happen to be.

I started exploring this model after watching the cost of skilled manual work rise in Bulgaria, where I live. While more people are attracted to careers that can be done behind a laptop, there is still plenty of work that simply cannot be moved online — you can’t renovate a bathroom, install a floor or replace a window over Zoom. The shortage of people willing and qualified to do this work can create an interesting opportunity for entrepreneurs who know how to connect local demand with reliable crews.

The same pressure is visible in the U.S. According to R&J, the construction industry needs to attract an estimated 349,000 net new workers in 2026 just to meet demand for construction services, with another 456,000 needed in 2027. The lesson I’ve learned is that running a business remotely doesn’t mean the business itself has to be digital. If you can build the systems for generating leads, handling customers and dispatching dependable teams, even a very hands-on local service business can be managed while you travel.

5. Keep a professional workspace without being tied to one location

Not every great vacation destination is a great place to work. I’ve traveled to places where finding a quiet, professional environment was surprisingly difficult. The few coffee shops available might be packed with families and screaming children or groups having beers in the middle of the day — not exactly the environment you want when you need three hours of uninterrupted work.

That’s why I now consider the availability of reliable coworking spaces when choosing where to stay. Coffee shops are fine for answering emails or handling a few simple tasks, but when I need to concentrate, take calls or make important decisions, I want somewhere that actually feels like an office.

According to Winston Tower, 45% of workers rate their productivity as excellent in a coworking environment, compared with just 27% when working from home. You can imagine that working from a hotel lobby, hotel room or coffee shop would be even worse than working from home. A little research before booking your destination can therefore make a big difference: Check the coworking spaces and flexible offices nearby, their opening hours and reviews.

Traveling gives you the freedom to work from almost anywhere, but that doesn’t mean you should try to work from everywhere. Just make sure there are a few good coworking spaces nearby.

6. Optimize your transportation when traveling

One thing I’ve learned from traveling is that the best way to get around changes completely from one country to another. In parts of Southeast Asia, for example, private drivers can be affordable enough that I hire the same driver for most or even all of my stay. He meets me at the airport, takes me to the hotel and is available when I need to move around, saving me the hassle of constantly arranging transportation. In Spain, I do almost the opposite: high-speed trains make traveling between major cities so convenient that a car often makes little sense.

New York taught me that timing matters just as much as the type of transportation you choose. Traffic can change dramatically depending on the hour, so I try to plan meetings and transfers around peak periods rather than automatically jumping into a car. According to BCS, during New York’s evening rush hour, driving 10 kilometers takes about 31 minutes, with an average speed of only around 19 km/h.

When I travel, I research not only whether trains, public transit, taxis or private drivers make the most sense, but also when I should use them. Saving 30 minutes here and an hour there adds up quickly when you’re trying to run a business at the same time.

7. Choose destinations that help you recharge

The way I travel has changed as I’ve gotten older and taken on more responsibility as a business owner. In my twenties, a good trip might have meant nightlife, parties and trying to squeeze as much as possible into every day. Today, I’m much more interested in coming back from a trip feeling better than when I left.

Especially during the winter, I like destinations with good spas and wellness facilities, where I can structure my day around three things: focused work first, a workout at the gym afterward and finally, recovery in a warm pool, sauna or spa. Apparently, I’m not alone in making that shift. According to Carbon Wellness, 56% of travelers say their number one motivation for leisure travel is to rest and recharge.

When you’re running a business while traveling, that balance becomes even more valuable. I can still get several productive hours of work done, but instead of ending the day exhausted after sightseeing and nightlife, I use the rest of the trip to exercise, recover and actually switch off.

8. Turn downtime into learning time

I used to listen to far more podcasts than I do today, with my listening probably peaking during the Covid years. Now I’m more selective about both what I listen to and when. Traveling creates some of the best opportunities: If I’m driving alone, doing a relatively easy workout or simply have an hour to myself while my family is somewhere else in the hotel or spa, I’ll often put on a business or entrepreneurship podcast. I use that time to hear how other founders think, discover new strategies or get a different perspective on something I’m already working on.

And this habit is common among other entrepreneurs: According to Castos, 43% of business owners and executives surveyed said podcasts were their primary source of information. I don’t feel the need to consume business content every free minute anymore, but podcasts are an easy way to turn some of the natural downtime that comes with traveling into useful learning without opening a laptop.

9. Let data tell you when your business needs attention

One of the biggest mistakes I can make while traveling is constantly checking whether everything is okay back home. I don’t want to spend half my trip messaging my team to ask how many leads came in, how campaigns are performing or whether sales are moving in the right direction. Instead, I prefer having the important numbers available in dashboards so I can quickly see what is happening and only step in when something actually needs my attention.

According to Magnific, 76% of firms say having sales data available in real time is very or extremely important for decision-making and business performance. For businesses with larger volumes of constantly changing information, real-time data infrastructure can take this further, allowing tools and dashboards to update as new activity happens rather than relying on yesterday’s reports. The better visibility I have into my businesses, the less I need to micromanage them — and that becomes especially valuable when I’m traveling.

10. Combine business travel with leisure

Whenever possible, I try to give my trips more than one purpose. If there’s an interesting conference in Spain, Thailand or Vietnam, for example, that can become the starting point for a longer trip. I’ll attend the event, arrange meetings with clients or business partners who happen to be in the region, and then leave several days for actually enjoying the destination.

I also sometimes do the reverse: Once I know where I want to travel, I look through my network to see whether there are clients, partners or worthwhile industry events nearby. This approach has become common enough to have its own name — “bleisure” travel.

According to Nobl Travel, 36% of global travelers plan to extend a business trip to enjoy leisure time before or after their work obligations. For me, combining the two makes the economics of traveling better, but more importantly, it turns a single trip into an opportunity to strengthen business relationships while still having a real vacation.

11. Create a “minimum viable workday”

When I’m traveling, I don’t try to recreate my normal workday in a hotel room, but I’ve also learned that completely switching off isn’t always realistic when you run a business. According to Tailor Brands, 85% of small business owners continue working in some capacity while on vacation. I’m usually part of that majority. I create what I call a “minimum viable workday.”

I identify the two or three things that genuinely need me and focus only on those. The key is cutting everything around the actual work. According to WPX, employees spend around 60% of their time on “work about work,” such as communicating about tasks, searching for information and chasing updates. When I’m traveling, I try to eliminate as much of that as possible. I handle the important decisions, solve anything urgent and then close the laptop — the business keeps moving, but I still get to enjoy the trip.

Running a business while traveling is ultimately about finding the right balance. You need systems, a reliable team and technology that keep things moving without your constant involvement, but you also need the discipline to know when to close the laptop. I’ve learned to focus on the work that genuinely needs me, automate or delegate the rest, and plan my trips in ways that make both working and relaxing easier. Do that well, and travel doesn’t have to interrupt your business — it can simply become part of how you run it.

Let me tell you a quick story.

There was a new town in Norway back in the 1990s, built by a rich oligarch who decided to create a new settlement and live there. For about five years after the town was created, houses there kept catching fire. Firefighters would come, put out the fire, go home and come back the next time. They even hired more firefighters and extinguished more fires.

Now, this was a cold town. Fires breaking out every other day made no sense. Everyone was asking, “How do we fight this fire better?” Eventually, one of the residents got sharp and asked a different question: “Why does this fire keep breaking out, and how do we stop it from happening in the first place?”

What they found: The contractor who built the town had used a thin, highly flammable material above the bricks for soundproofing in every room, including the kitchens. Every kitchen in every house was basically a fire waiting to happen. The fix was simple: Break into every kitchen and remove that layer. They also installed a device in every home that alerted the fire station the moment smoke was detected. We know it today as a smoke alarm.

After fixing the root cause, the fire outbreaks stopped entirely.

That’s systemization thinking. The firefighters were working hard and thought they were killing it. But working hard inside a system that could be fixed is not efficient. A sharp person sees the difference.

That story is fictional, but you get the point.

So what is systemization thinking?

Systemization thinking is the habit of seeing things as systems instead of isolated events.

Instead of asking, “How do I solve this problem right now?” You ask, “What process, structure or mechanism can solve this repeatedly, with less effort, every time it comes up?”

A normal thinker looks at slow customer support, for example, and says, “Let’s reply faster.” A systemization thinker asks why support is slow in the first place, then builds templates, routing rules and automations so that speed becomes automatic and doesn’t depend on anyone trying harder.

1. Everything is a process

Every repeated outcome, good or bad, comes from a process, whether you designed it intentionally or not. Employees always late? Customers always confused? Same bugs recurring? Probably a systems issue.

The instinct most people have is to blame the people. The sharper instinct is to ask what system produced this outcome, and then fix the system.

2. Stop solving the same problem three times

If you’ve fixed something manually three times, that’s a sign it needs a permanent solution, not a fourth manual fix. Don’t rely on memory or on someone being available.

I spoke with someone who used to work at McDonald’s. On his first day, he was already making burgers, even though he’d never cooked before. McDonald’s doesn’t rely on talented burger makers. It relies on a system and a simple checklist. The system produces the burger, not the person’s natural ability. That’s systemization.

3. Repeatability beats genius

A genius one-time result is less valuable than an average result that happens reliably every time.

A few years ago, we were living somewhere far from the city, and finding a maid was nearly impossible. No public transport reached there, and no maid was going to take an Uber to work every day. Person after person came for the interview, saw how far it was and never came back.

Then one woman came in, started the job and kept coming. She’d gone on a Facebook group full of drivers and negotiated a deal: same driver, morning and evening, fixed monthly rate. She identified the problem, built a repeatable solution and executed it. We kept her. That kind of thinking is what separates someone who survives a difficult situation from someone who just complains about it.

4. Think in inputs → process → outputs

When something goes wrong, don’t just look at the outcome. Trace it back. Bad app reviews? Instead of “users are angry,” ask: What inputs caused this? Where did the process fail? What metrics would have revealed this earlier? Find where the system broke, not just where the pain showed up.

5. Don’t be busy, be efficient

Busy means you’re always doing something. Efficient means what you’re doing actually produces the best result in the least amount of time.

For example, if I had about 940 software programs to review, I could write a document on how they should be reviewed and assign someone to review them one by one. The person would be extremely busy. Instead, that same document could become an AI skill that does the review 100x faster, and the assigned person would only review the shortlist manually for quality assurance.

Busy feels productive, but if at the end of the day the output doesn’t match the hours, the hours don’t matter. A lot of what people call “hard work” is really just an inefficient system that nobody has bothered to fix. “Work smarter, not harder” is a cliché because it’s true.

The hard part of systemization

People think once you build a system, the problem is solved. Not every time. A system itself has to be maintained, enforced, monitored and improved. SOPs are the most common form of systemization, and they’re genuinely difficult to keep alive. You’ll write a really good one and feel good about it, then six months later, realize nobody is following it, nobody has updated it and the team has quietly gone back to doing things the way they want.

A badly designed or poorly enforced system can create more work than no system at all. And a system that lives only in a document nobody opens is not a system; it’s just writing.

This is why culture matters more than any individual system. Systemization requires proactivity: People have to see a problem before it becomes a crisis, care enough to build a lasting solution and resist the easier option of just handling it manually again.

The summary

Stop solving the same problem more than three times. When something keeps breaking, fix the system, not just the symptom. Build processes that work without a single point of failure. And remember, a system is only as good as the culture that maintains it.

Let me tell you a quick story.

There was a new town in Norway back in the 1990s, built by a rich oligarch who decided to create a new settlement and live there. For about five years after the town was created, houses there kept catching fire. Firefighters would come, put out the fire, go home and come back the next time. They even hired more firefighters and extinguished more fires.

Now, this was a cold town. Fires breaking out every other day made no sense. Everyone was asking, “How do we fight this fire better?” Eventually, one of the residents got sharp and asked a different question: “Why does this fire keep breaking out, and how do we stop it from happening in the first place?”

My parents’ generation largely grew up believing you found a good company, worked hard, moved up the ladder and, if everything went according to plan, stayed there.

Today, people change jobs for better pay, flexibility, titles and that elusive thing every company claims to have — great culture. At the same time, we’ve raised a generation accustomed to immediacy. Order something today, and it might arrive today. Want to watch something? Stream it. Need an answer? Ask AI.

That changes consumers, employees and entrepreneurs.

Some of the old startup playbook focused on things that looked good: elaborate offices, cool perks, corporate initiatives and, for a while, apparently putting a slide in the middle of the office. None of that compensates for getting the fundamentals wrong.

Building a company now requires constantly questioning what those fundamentals should be.

1. Use AI to compete with AI

A good friend owns a marketing company and is an incredible graphic designer. Her custom, hand-drawn work is head and shoulders above the generic AI material we’re seeing everywhere. But she’s competing with something that can produce an image in seconds.

Customers may recognize that her work is better and still ask: Why should I pay more and wait longer when AI can give me something good enough right now?

My question to her was: Why not offer both?

Let AI handle what doesn’t require her talent, then apply her creativity and judgment where they actually change the result. If AI turns a 20-hour job into a two-hour job, eventually the economics change too. Someone will deliver faster or cheaper.

You’re not just competing with AI. You’re competing with the entrepreneur who learns to use it better than you.

2. Rethink the job before you hire for it

Another friend is an accounting director at a Fortune 500 company. Her company is reconsidering certain titles, degree requirements and experience expectations while simultaneously pushing employees to use AI. AI utilization is even becoming part of how performance is evaluated.

Think about where that could lead. An accountant may spend less time producing information and more time validating it, finding errors and deciding what it means.

Eventually, AI may become good at some of that too. We don’t know. That’s why entrepreneurs shouldn’t automatically recreate yesterday’s job descriptions.

Before hiring, ask what actually needs to be accomplished. Can technology do part of it? Can you eliminate the process altogether? Can one exceptional employee with the right technology accomplish what once required three?

Design the job around the work that exists today.

3. Build a multigenerational company — and listen to it

A 22-year-old employee grew up in a completely different consumer environment than someone who’s 55. They may instinctively understand platforms, expectations and behaviors an older executive had to learn.

The 55-year-old may have lived through recessions, hiring booms, layoffs, management trends and supposedly revolutionary technologies that disappeared five years later.

Hire both. More importantly, listen to both.

Your youngest employee may recognize where customers are going before you do. Your most experienced employee may recognize a mistake because they’ve already watched somebody make it.

Different generations aren’t just a workforce statistic. Their collective experience can be a competitive advantage.

4. Recognize that “instant” has changed your customer

Customers no longer compare your service only to your direct competitors. Amazon delivers the same day. Netflix streams instantly. Uber shows exactly where your driver is. AI answers a question in seconds.

Then a company says, “We’ll get back to you in three to five business days.” That increasingly feels ridiculous.

Not every business needs to operate at Amazon speed, and speed doesn’t excuse bad work. But immediacy has changed what good service feels like.

Friction is now part of your product whether you intended it to be or not.

5. Don’t assume AI can’t replace you

There’s a comforting prediction about AI: Great designers, accountants, lawyers, marketers and engineers aren’t going anywhere.

Maybe. I wouldn’t bet my company on it.

Instead of defending the old way of doing something, ask what happens if technology becomes dramatically better at it. Could you build the technology that makes an old process obsolete instead of being the person defending that process?

Then ask a harder question: What should technology replace?

We assume removing human involvement makes something less human. But technology’s purpose shouldn’t be preserving jobs or eliminating them. It should be improving outcomes for people.

Entrepreneurs should be willing to follow that question wherever it leads.

6. Invest in what technology makes more valuable

If practically anyone can generate an article, advertisement, logo or marketing campaign in minutes, simply producing something competent isn’t much of an advantage.

So what remains scarce? Trust. Relationships. Reputation. Judgment. Taste. Community. Original ideas. Exceptional service.

And human connection.

In a world filled with automated interactions and synthetic content, genuine relationships may become more valuable.

Don’t only ask what AI commoditizes. Ask what becomes more valuable because everything else has been commoditized.

7. Think for yourself

“We’ve always done it this way” has always been dangerous in business. But calling yourself a “disruptor,” “innovator” or “cutting-edge” isn’t particularly meaningful anymore either.

Maybe thinking for yourself is disruptive enough. Do you need an office? Does that position require a degree? Does the customer care about that feature? Does this meeting need to happen? Does a human need to perform that task?

And keep asking.

The opportunity isn’t to build the company someone taught you to build and sprinkle AI on top. It’s to reconsider what the company itself should look like.

It might have 100 employees. It might have 10. It might automate something competitors still do manually while investing heavily in people somewhere everyone else is automating. The answer isn’t always more AI.

Every generation of entrepreneurs inherits rules from the generation before it. The smartest ones figure out which are still worth following.

My parents’ generation largely grew up believing you found a good company, worked hard, moved up the ladder and, if everything went according to plan, stayed there.

Today, people change jobs for better pay, flexibility, titles and that elusive thing every company claims to have — great culture. At the same time, we’ve raised a generation accustomed to immediacy. Order something today, and it might arrive today. Want to watch something? Stream it. Need an answer? Ask AI.

That changes consumers, employees and entrepreneurs.

As the side hustle era continues, AI keeps adding to the number of lucrative opportunities available. 

Nearly 70% of Gen Z side-hustlers said they consider AI the go-to resource when they need help in work, according to a recent report from Samsung. 

So it’s perhaps not surprising that many people who want to earn money on the side leverage AI from the jump — even charging for jobs that hinge on the technology. 

But which AI side hustles come with the best payout? NetCredit analyzed publicly available freelancer rates on Fiverr, filtering for a 24-hour delivery time, to find out. 

Three AI side hustles tied for the highest-paying title. AI spokesperson videos, which feature digital avatars delivering scripts on camera, bring in a $100 median rate for tasks completed within 24 hours, per the research. 

Side-hustlers offering services related to AI applications or generative AI lessons typically see the same amount.

Side gigs adjacent to ChatGPT applications and AI integrations snagged the fourth and fifth spots, with median rates for 24-hour jobs landing at $87.50 and $62.50, respectively. 

Read on for NetCredit’s full list of the best-paying AI side hustles for a single day of work:

As the side hustle era continues, AI keeps adding to the number of lucrative opportunities available. 

Nearly 70% of Gen Z side-hustlers said they consider AI the go-to resource when they need help in work, according to a recent report from Samsung. 

So it’s perhaps not surprising that many people who want to earn money on the side leverage AI from the jump — even charging for jobs that hinge on the technology. 

But which AI side hustles come with the best payout? NetCredit analyzed publicly available freelancer rates on Fiverr, filtering for a 24-hour delivery time, to find out. 

Three AI side hustles tied for the highest-paying title. AI spokesperson videos, which feature digital avatars delivering scripts on camera, bring in a $100 median rate for tasks completed within 24 hours, per the research. 

Side-hustlers offering services related to AI applications or generative AI lessons typically see the same amount.

Side gigs adjacent to ChatGPT applications and AI integrations snagged the fourth and fifth spots, with median rates for 24-hour jobs landing at $87.50 and $62.50, respectively. 

Read on for NetCredit’s full list of the best-paying AI side hustles for a single day of work:

“Hell is other people,” Jean-Paul Sartre wrote in No Exit. Philosopher Kiki Berk examines the phrase in her analysis of Sartre’s view of personal relationships. It does not simply mean that other people are unpleasant or responsible for our unhappiness. It describes what happens when another person looks at us and turns us into an object inside their consciousness.

They interpret our behavior, assign motives to our actions and create a version of us that exists independently of the person we believe ourselves to be. You may be generous and still appear selfish, remain silent and appear weak, or speak confidently and appear arrogant. You can explain yourself, improve your performance and try to correct the judgment, but you can never enter another person’s mind and arrange your image exactly as you wish. Their perception remains outside your control, yet much of your identity may still depend on receiving the right verdict from it.

The identity trap

Jennifer Crocker and Katherine Knight write that self-esteem depends on “what people believe they need to be or do to have worth as a person” in Contingencies of Self-Worth. This is the real danger of labels. Once your worth depends on being a founder, writer or leader, an ordinary setback stops being an event and becomes evidence against who you are.

Anlan Zheng, Brittany Duff, Patrick Vargas and Mike Yao found that people “choose to share things that are self-enhancing” in their research on social-media self-presentation. That habit does not remain online. We begin observing ourselves while we work, travel, learn and build, asking what each activity says about us instead of whether the activity itself matters.

Ryan Holiday’s title Ego Is the Enemy makes the diagnosis explicit, while its publisher describes successful figures as “conquering their own egos.” I agree with the warning more than the title. Ego can support ambition, but it becomes dangerous when the appearance of work replaces the work and recognition becomes more important than knowledge.

Daphna Oyserman writes that “identities are dynamically constructed in context” in her work on identity-based motivation. We are obsessed with nouns rather than verbs. We do not simply want to build; we want to become founders. We do not simply want to write; we want to become writers. We do not simply want to lead; we want to be recognized as leaders. The action is no longer sufficient. It must produce a title, and the title must then be protected.

Once “founder” becomes who you are, a failed product is no longer merely a failed product. It threatens the identity itself. Oyserman explains that identity shapes how people interpret difficulty in the same research. The harder you work to preserve the noun, the easier it becomes to interpret ordinary setbacks as proof that you do not deserve it.

Put the verb first

Richard Ryan and Edward Deci write that “social environments can facilitate or forestall intrinsic motivation” in their foundational paper on self-determination theory. Putting the verb first changes the environment inside your own mind. Building matters more than looking like a founder. Writing matters more than being recognized as a writer.

The noun asks the world for confirmation, whereas the verb returns you to action. When the noun comes first, you build to prove that you are an entrepreneur. When the verb comes first, you build because a problem deserves a solution. One protects an image. The other creates value.

But every verb still needs a subject. Someone builds, writes, teaches and leads. Adam Grant writes that prosocial motivation can promote “high levels of persistence, performance, and productivity” when intrinsic motivation is also high in Does Intrinsic Motivation Fuel the Prosocial Fire? I call that subject the giver: the person who builds because a problem deserves a solution and writes because an idea deserves form.

Why the giver is different

Crocker and Knight call contingencies of self-worth “areas of psychological vulnerability” in their research. A founder needs a company, a writer needs work and a leader needs recognition of the role. Each identity contains a condition that must repeatedly be satisfied. The giver can build today, teach tomorrow and listen the day after without losing the central subject.

Mark Bolino and Adam Grant define prosocial motivation as “the desire to benefit others or expend effort out of concern for others” in their review of prosocial work. That direction makes the giver less sensitive to ego. Instead of asking, “Do I still deserve this title?” the giver asks, “What can I contribute here?” The identity rests less on a category and more on the movement of the action.

The risk of performing generosity

Ryan and Deci describe intrinsic motivation as behavior that is “inherently interesting and enjoyable” in their research. Giving can lose that autonomy when it becomes a performance. You can help to feel indispensable, mentor to be admired or sacrifice so that others feel indebted. You can give while still asking.

The solution is not to abandon the giver identity but to define it carefully. Grant suggests that contribution is more sustainable when the action itself remains meaningful. Before acting, ask whether you are creating value or protecting an identity, whether you would still act if nobody knew and whether the action feels complete without recognition.

Kiki Berk writes that Sartre’s philosophy does not exclude “an ethics of deliverance and salvation” in her discussion of No Exit. You may never control the person you become in somebody else’s mind, but you can stop making that person the place where your work becomes complete. Stop trying to look like a founder. Build. Stop trying to look like a leader, and instead, actually lead. Choose the verb, define the giver carefully and let contribution, instead of recognition, become the center of your mindset.

“Hell is other people,” Jean-Paul Sartre wrote in No Exit. Philosopher Kiki Berk examines the phrase in her analysis of Sartre’s view of personal relationships. It does not simply mean that other people are unpleasant or responsible for our unhappiness. It describes what happens when another person looks at us and turns us into an object inside their consciousness.

They interpret our behavior, assign motives to our actions and create a version of us that exists independently of the person we believe ourselves to be. You may be generous and still appear selfish, remain silent and appear weak, or speak confidently and appear arrogant. You can explain yourself, improve your performance and try to correct the judgment, but you can never enter another person’s mind and arrange your image exactly as you wish. Their perception remains outside your control, yet much of your identity may still depend on receiving the right verdict from it.

The identity trap

Jennifer Crocker and Katherine Knight write that self-esteem depends on “what people believe they need to be or do to have worth as a person” in Contingencies of Self-Worth. This is the real danger of labels. Once your worth depends on being a founder, writer or leader, an ordinary setback stops being an event and becomes evidence against who you are.

Last year, I spent time with a leadership team that had scaled into four international markets faster than almost any company I’d worked with. The numbers looked strong, headcount was growing, the pipeline was building and the board was happy.

But something felt off to the CEO, and when we dug into it, the problem was hard to name at first. Regional teams were hitting their local targets but felt disconnected from each other. Decisions that should have been straightforward were taking weeks because nobody was sure who had authority. The global culture the founders had worked hard to build back home was, in the words of one regional director, “kind of theoretical out here.”

That phrase stuck with me. Kind of theoretical out here. It’s a polite way of saying: We heard your values; we just don’t see them in how we’re actually structured.

Scaling globally is one of the few challenges in business where the things that made you successful domestically can actively work against you if you don’t adapt how you lead.

Where most global expansions quietly break down

The instinct when scaling into new markets is to export the playbook. You take what worked, package it up and hand it to the regional team. For a while, often longer than you’d expect, things seem fine. Teams are executing, metrics are moving and the model appears to be transferring.

What’s actually happening underneath is that your regional leaders are adapting the playbook to local reality without telling you, because telling you would mean admitting the original version doesn’t fit. So they nod in the all-hands and quietly do something different in the market. By the time the gap becomes visible, you’ve got multiple unofficial versions of your own company operating simultaneously.

This isn’t a hiring problem or a communication problem, though both tend to get blamed. When a centralized playbook meets a local market and there’s no formal mechanism for the regional team to say “this part doesn’t work here,” adaptation goes underground. And underground adaptation is how you end up with a brand that means different things in different places.

The useful distinction is being precise about what actually has to be uniform versus what can flex. Your positioning and core values need to be consistent everywhere. The way you generate pipeline or onboard a new hire can legitimately vary by market, and pretending otherwise doesn’t protect your standards, it just frustrates the people trying to meet them.

What your regional leaders aren’t telling you

One of the underrated costs of rapid global expansion is information asymmetry. Your regional leads are watching competitor behavior you can’t see from headquarters, picking up on buyer sentiment shifts before they show up in your numbers and understanding the cultural subtext of what’s happening in their markets in ways that don’t translate cleanly into a quarterly report.

Whether that intelligence reaches you depends almost entirely on whether your environment rewards honesty or punishes it. I’ve worked with plenty of regional leaders who had real concerns about the global strategy and kept them to themselves because raising issues with headquarters felt professionally risky. The gap between what gets said in regional check-ins and what regional leaders actually believe is often wider than anyone at the center realizes.

Getting that intelligence to flow requires two things working together. Regional leaders need to be part of strategy conversations before decisions are made, so their input can actually shape direction rather than just critique it after the fact. And leadership at the center needs a track record of visibly responding to that input in ways the regions can see and point to. Without that track record, inviting feedback is just theater.

Building culture across time zones

The real test of whether you’ve built a global culture or just a global company is what happens when you’re not in the room. Anyone can hold culture together when they’re physically present, running the all-hands and setting the tone in every meeting. The question is: What happens in your London office on a Thursday morning when a difficult situation comes up and it’s 2 a.m. where you are?

The leaders who get this right stop trying to be present everywhere and start investing in the people who already are: regional leaders and senior people on the ground who genuinely carry the company’s values and have the credibility to model them without it feeling like a directive from headquarters. You’re distributing cultural judgment rather than transmitting cultural instructions, which requires a fundamentally different relationship with your regional leadership.

That kind of judgment doesn’t develop through documentation. A values deck can articulate the principles, but it can’t build the shared context that makes those principles feel real. What builds that context is people across regions working through hard problems together, not just syncing on status in a weekly standup. The strongest global cultures I’ve seen are built on a history of shared difficulty, teams from different markets collaborating on something genuinely challenging and coming out the other side with a common reference point.

Holding vision tight, holding execution loosely

The leaders who scale globally without losing themselves tend to have a clear sense of what they’re actually trying to preserve. They’re not trying to replicate the exact form of what they built at home. They’re trying to extend its intent into a new context, which requires trusting people who understand that context better than they do.

That trust is genuinely hard when you’re attached to how things have worked so far. The original model was built for a specific environment, with specific customers, in a specific competitive landscape. Holding onto it past the point where it fits isn’t protecting your culture; it’s limiting the people trying to carry it forward.

The global leaders who get this right hold their vision with conviction and their execution with enough flexibility to let regional teams actually own their markets. Getting that balance right is most of the work.

Last year, I spent time with a leadership team that had scaled into four international markets faster than almost any company I’d worked with. The numbers looked strong, headcount was growing, the pipeline was building and the board was happy.

But something felt off to the CEO, and when we dug into it, the problem was hard to name at first. Regional teams were hitting their local targets but felt disconnected from each other. Decisions that should have been straightforward were taking weeks because nobody was sure who had authority. The global culture the founders had worked hard to build back home was, in the words of one regional director, “kind of theoretical out here.”

That phrase stuck with me. Kind of theoretical out here. It’s a polite way of saying: We heard your values; we just don’t see them in how we’re actually structured.

The COO had every reason to believe the launch problem was fixed. A regional product launch had missed its date by six weeks after a late packaging spec change got caught in a slow approval path.

Marketing needed speed to protect the launch date. Procurement needed enough review to protect spend discipline and vendor risk.

The COO resolved the conflict with a simple rule. Any launch-critical vendor expedite fee below a defined cap would receive same-day procurement approval, while anything above the cap would still go through the normal review.

On the next comparable launch, the same kind of packaging issue appeared. The request went in on a Tuesday, procurement approved it that afternoon, and the launch hit its date.

The fix worked exactly as intended.

The evidence looked conclusive

The turnaround on that type of launch-related request moved from 11 days to same-day. The launch stayed on schedule, and nobody had to escalate, negotiate across functions or quietly absorb the cost somewhere else.

Leadership now had something far more persuasive than a new policy. It had proof that the intervention worked.

That matters because leaders should look for evidence that a fix has changed the result. If a problem caused a six-week delay and the next comparable case moved cleanly, concluding that the failure point has been addressed is reasonable.

The risk sits inside what happens next. The organization starts treating evidence that one failure point has been fixed as evidence that the underlying problem has been fixed.

In this case, the deeper problem was the conflict between two legitimate priorities. Marketing was protecting launch speed, while procurement was protecting spend discipline and vendor risk.

The packaging approval was simply the first place where those priorities collided hard enough to become visible. The COO’s rule fixed that collision, but it didn’t remove the conflict.

A successful fix narrows the search

Once the packaging issue stopped recurring, leadership had little reason to keep looking for the same problem. That’s precisely what makes this kind of execution problem difficult to see.

The same conflict between launch speed and spend discipline still exists at other decision points. Rush freight has its own approval path, fulfillment overtime sits somewhere else, and last-minute creative reprints may involve another budget and another set of people.

Each issue looks different when it arrives. A rush freight request looks like logistics, overtime looks like a staffing or cost decision, and a creative reprint looks like a marketing expense.

None automatically points back to a packaging approval that leadership already considers solved. Yet each decision contains the same question: When protecting the launch date costs more money, which priority gives way?

The packaging rule answers that question in one place. It says nothing about the others.

That’s how a successful fix makes the larger structural problem harder to see. The visible failure disappears before leadership has established where else the same conflict exists.

The same conflict starts wearing different labels

When the next collision appears, it doesn’t arrive labeled as a repeat of the packaging problem. It arrives with different people, different language and a different operational consequence.

The freight decision may be escalated through supply chain, the overtime question may sit with fulfillment, and the reprint decision may remain inside marketing. From leadership’s perspective, those look like separate issues.

That matters because separate issues produce separate responses. One decision gets handled as freight, another gets handled as labor cost, and another gets treated as a print expense.

The organization ends up resolving the same underlying tradeoff several times, one decision point at a time, without seeing that those decisions belong together. Nothing about the local responses has to be wrong.

They may solve each immediate problem just as effectively as the COO’s packaging rule solved the first one. Each successful local answer then removes another reason to connect the issue back to the broader conflict.

The organization gets better at solving the visible manifestations while remaining unaware that the same tradeoff keeps generating them. That’s what makes the pattern persistent.

This is one way hidden problems persist even in organizations that respond quickly when something goes wrong. The problem isn’t hidden because leaders are indifferent. It’s hidden because each visible expression gets resolved well enough to make further investigation feel unnecessary.

The fix is not the failure

It would be easy to turn this into an argument against narrow fixes. That would be the wrong conclusion.

The COO’s rule was a good decision. It solved the packaging approval problem, reduced turnaround time and protected the next launch.

There’s no reason to criticize a fix for doing exactly what it was designed to do. The leadership risk comes afterward, when evidence that one collision has been resolved becomes evidence that the underlying conflict has been resolved.

A bounded fix proves that one decision point is now working. It doesn’t prove that every other place where the same priorities meet has already been settled.

That distinction becomes more important as organizations become larger and work becomes more distributed. The same two priorities may collide in several functions, regions or approval paths without any single leader seeing those decisions together.

One function solves its version while another solves a different version, and both report progress. The organization can therefore improve at several individual points while still carrying the same unresolved conflict across the system.

Success closes the question too early

Leaders spend a great deal of time worrying about fixes that fail. Failed interventions stay visible because escalations continue, results remain poor, and everyone knows the work is unfinished.

Successful interventions create the opposite signal because the escalation disappears, the metric improves, and the next comparable case moves cleanly. Leadership has credible evidence that action produced the intended result.

That’s normally what good execution looks like. But when the visible failure was only one expression of a broader cross-priority conflict, success at that point doesn’t tell leaders where else the conflict remains.

It only tells them that this particular collision has been resolved. The more convincing that evidence becomes, the easier it is to stop asking a different question.

Not whether the fix worked. It did.

The question is whether what was fixed was the problem itself, or simply the first place the problem became visible. Both produce the same reassuring short-term result: The next case works. Only one means the search is actually over.

The COO had every reason to believe the launch problem was fixed. A regional product launch had missed its date by six weeks after a late packaging spec change got caught in a slow approval path.

Marketing needed speed to protect the launch date. Procurement needed enough review to protect spend discipline and vendor risk.

The COO resolved the conflict with a simple rule. Any launch-critical vendor expedite fee below a defined cap would receive same-day procurement approval, while anything above the cap would still go through the normal review.

Most executives assume their track record will carry them through interviews, but in reality, the leadership instincts you’ve spent years refining can actively hurt you when you’re a candidate.

I see this pattern regularly in my interview coaching practice. Accomplished leaders often walk out of interview loops confused about why the offer went to another candidate. The truth is, their qualifications were never the issue. Instead, the issue was that they interviewed the way they lead, and although leading this way serves them well day-to-day, it’s costing them opportunities in the interview room.

Let’s explore the three leadership instincts I most often see working against executives in interviews, as well as how to adjust each one.

1. You give your team all the credit

Great leaders distribute praise to their team. When a project succeeds, they spotlight the people who did the work, and over time, “we” becomes their default language. This habit builds trust and loyalty when you’re leading a team, making you look like a secure, selfless leader, but when you’re interviewing, it creates a major problem.

Employers are hiring only one person: you. When every story is told in “we” language, interviewers are left guessing about your individual contributions. Some interviewers will assume you’re being modest. Others will conclude you were just along for the ride and didn’t drive the results yourself. Neither assumption helps you, particularly when you’re competing against equally qualified candidates who more clearly communicate their impact.

I recall working with a product management executive who kept advancing to final rounds but never receiving an offer. When he requested feedback, one panel shared that they struggled to pinpoint what he had personally contributed to his team’s wins. We reworked his stories to name the specific decisions he had made, as well as the initiatives he had personally led, and he received an offer shortly after.

In my experience coaching hundreds of leaders through executive interviews, the fix isn’t to take credit that rightfully belongs to your team. Instead, it’s to continue calling out their contributions while also being clear about your own. For each interview story, identify your individual role or what would have gone differently without you. That is the part interviewers need to hear in the first person. This might sound like, “My team delivered an incredible product launch. My role was making the call to delay the release by two weeks, which protected the customer experience and helped us renew every one of our major accounts.”

2. You assume your scope speaks for itself

Inside your company, everyone shares context. Your colleagues already know how complex your organization is and why a particular initiative was challenging. Because of this, you don’t need to explain the backstory behind your work when you’re communicating internally.

But interviewers don’t share that context, and when executives compress a major accomplishment into a single sentence, their achievement arrives without the stakes that made it impressive. “I led the AI transformation effort” means very little to someone who doesn’t know that adoption had stalled twice before or that the board had made it the company’s top priority.

One of my clients, an operations executive, described a two-year turnaround in a single sentence during our coaching sessions. It sounded routine until we unpacked the situation he had walked into, including millions of dollars in sunk costs and a system that multiple predecessors had failed to fix. Once he named those stakes in interviews, the same accomplishment landed more powerfully.

I coach leaders to highlight the stakes around each story. You don’t need to craft a dramatic screenplay like Shonda Rhimes, but you do need to set the scene. Before your next interview, take your strongest accomplishments and answer these questions about each one: What was at stake if this failed? What did the before and after look like? While these answers are likely already obvious to you, saying them out loud turns a resume bullet point into a memorable story and sets you apart from other candidates.

3. You’ve mastered diplomatic communication

Senior leaders are often trained by experience to hedge in public. You’ve likely learned to build consensus before taking a stand and acknowledge diverse stakeholder perspectives before committing to your own. This is how you usually gain alignment and trust, but in an interview, it can backfire and sound like you don’t have a point of view.

Companies hire executives for their discernment. When you answer a strategic question with carefully balanced considerations and no conclusion, interviewers walk away unsure whether you can commit to a direction. Even worse, some will conclude that you’re a leader who waits to see where the group lands before speaking up.

I recently worked with an IT executive who had pushed back when his CEO wanted to move forward full throttle on an AI transformation. He worried that the story would make him sound difficult, so in interviews he softened the details until his position disappeared entirely. Once we reworked the story so that he stated his stance and the reasoning behind it upfront, the feedback changed. Interviewers began commenting on his sound judgment and asking thoughtful follow-up questions about how he had managed the disagreement.

The adjustment I recommend is simple to describe but uncomfortable to practice: Lead with your position, then add the nuance. In my coaching sessions, we rehearse responses like, “Here’s my recommendation, and here’s what would change my mind.” This structure allows you to demonstrate conviction while remaining open to input, and it leaves interviewers confident that you can make the tough calls.

Your leadership instincts aren’t flaws. They helped you become the leader you are today, and you’ll need them again once you land your new role. The challenge is recognizing when you’re the candidate rather than the leader and adjusting how you communicate. This can be difficult to do on your own because your leadership habits have become second nature. With practice, whether by yourself or alongside a trained professional, you can learn to notice what interviewers hear that you no longer do. You’ve got this!

Most executives assume their track record will carry them through interviews, but in reality, the leadership instincts you’ve spent years refining can actively hurt you when you’re a candidate.

I see this pattern regularly in my interview coaching practice. Accomplished leaders often walk out of interview loops confused about why the offer went to another candidate. The truth is, their qualifications were never the issue. Instead, the issue was that they interviewed the way they lead, and although leading this way serves them well day-to-day, it’s costing them opportunities in the interview room.

Let’s explore the three leadership instincts I most often see working against executives in interviews, as well as how to adjust each one.