6 Hard Lessons: The Regrets Entrepreneurs Don’t Talk About (But Should)

Tony Hsieh, the late visionary behind Zappos, didn’t just know success — he learned some tough lessons along the way.

In his book, Delivering Happiness: A Path to Profits, Passion, and Purpose, Tony shares his story about the early days of his entrepreneurial journey, particularly his experience with LinkExchange, the internet advertising network he co-founded before Zappos.

It’s a story that resonates with anyone who’s ever started a business.

LinkExchange was one of those meteoric success stories — rapid growth, big money, everything an entrepreneur dreams about.

But as the company grew, Tony started to feel like something was off. Despite the soaring numbers and impressive growth, the company began to feel… well, different.

The excitement and passion that once fueled everything that Zappos did started to fade.

Tony puts it bluntly in his book: “I dreaded going to work. The excitement and passion were gone.” They were hiring rapidly, but many of the new faces didn’t quite grasp the original vision.

And suddenly, the company that had once been Tony’s pride and joy became a place he hated going to every day.

By 1998 — just two years after launch — LinkExchange had caught the eye of Microsoft. They came knocking with a $265 million offer, the kind of exit that most entrepreneurs would jump at. But for Tony, it wasn’t that simple. 

In his TED Talk, he got real about how selling the company wasn’t just about the money. Sure, the deal made him wealthy beyond his wildest dreams, but it also left him feeling empty.

Somewhere along the way, he realized he had lost sight of what really mattered to him.

The truth is..this isn’t just Tony’s story — it’s the story of so many entrepreneurs.

You pour your heart into building something with passion and purpose, only to watch it slip away, sometimes before you even realize what’s happening.

The emotional toll can be devastating. 

Our CEO at doola, Arjun Mahadevan, has heard countless similar stories from founders on his podcast:15 Minute Founder.

Their experiences echo Tony’s and serve as a reminder of the challenges entrepreneurs face. This is why it’s crucial to recognize these common regrets early on and take proactive steps to avoid them.

In this blog, we’ll explore six regrets that many entrepreneurs carry with them and, more importantly, how you can avoid them. Because if there’s one thing we’ve learned at doola, it’s that you don’t have to walk this path alone.

We believe that with the right support, you can navigate any challenge without losing sight of what really matters.

And in case you don’t know, doola helps global entrepreneurs set up a US LLC and keep tax compliant without the hassle!

So, let’s get started.

Regret#1 Losing Sight of the Mission

You know that moment when you’re deep into a project, and suddenly, you look up and realize you’ve drifted way off course? That’s what losing sight of your mission feels like. It happens slowly, almost imperceptibly.

One day, you’re fueled by this big, bold idea that keeps you up at night with excitement. The next, you’re buried in the day-to-day grind, and somehow, the passion you started with has taken a backseat to spreadsheets and meetings. 

It’s easy to get caught up in the hustle. The pressures of growth, profitability, and making sure everything doesn’t fall apart can be overwhelming.

This is a common challenge for many entrepreneurs who find themselves so focused on the business’s immediate demands that they lose touch with the very mission that inspired them in the first place.

Howard Schultz, former CEO of Starbucks, knew this feeling all too well. He once recounted how the company strayed from its original mission of creating a unique coffee experience.

As Starbucks expanded rapidly, it became more about numbers and less about the customer experience. Schultz noticed that the brand was losing its charm and authenticity, which was the very essence that made Starbucks special.  

It wasn’t an easy realization, but he knew that if Starbucks was going to stay true to its mission, something had to change.

So, he took steps to realign the company, bringing the focus back to quality and customer experience, rather than just expanding for the sake of growth.

How Can You Avoid This?

Here’s the thing: your mission is your Pole Star. It’s your guide to every decision, every new hire, and every campaign. But even the best of us can get lost along the way without regular check-ins. 

Three things you should diligently try to do when you feel like you are losing sight of your mission.

Revisit Your “Why” Regularly: Take some time off — whether it’s every quarter or even every month — to sit down and really think about why you started this whole company in the first place. This is a very preachy step, but try doing it religiously. It’ll help. Assess if what you’re doing today still aligns with your original mission. If not, it’s time to steer the ship back on course. 

For example, if you started your business to create eco-friendly products, but you’ve gradually shifted toward cheaper materials to boost profits, it’s time to ask yourself: “Is this why I started?” 

If the answer is no, then it’s time to refocus on sustainability and realign with your original mission. Regularly checking in with your “why” ensures your actions stay true to your purpose.

Embed Your Mission in Everyday Decisions: Your mission isn’t just a fancy and bold sentence on your website. It should be the heartbeat of your company. Before making big or small decisions, ask yourself and your team, “Does this align with our mission?” 

Culture Check-Ins: Think of your company culture like the soil that nurtures your mission. If the soil’s not right, nothing can grow.

Regularly check in with your team to see how they’re feeling about the work and the culture. Approach this candidly, like a friend. Are they still inspired by the mission, or has it become just another job?

Their responses will help you take specific actions for each of their problems.

You’re gonna love this: The Lifestyle of a Successful Entrepreneur: 17 Winning Habits

Regret #2 Ignoring Mental Health

Burnout: It’s that thing we all like to pretend we’re immune to, right up until it knocks us flat. 

And if you’re an entrepreneur, the pressure to keep pushing, keep grinding, can be relentless and violent.

But here’s the uncomfortable truth: ignoring your mental health and all the signs of burnout won’t just damage you — it can take down your business too.

We’ve all heard stories of entrepreneurs who’ve hit that wall, and it’s not just about the late nights or the stress. It’s about that moment when everything you’ve built feels like it’s crumbling because you’re too exhausted to hold it all together. Don’t let that happen to you.

Arianna Huffington learned this the hard way. You’ve probably heard her story on Huffington Post — she was powering through when she suddenly collapsed from exhaustion. That was her wake-up call. 

Arianna realized she was pushing herself to the brink, and it wasn’t sustainable. 

She made a change, not just for herself but for everyone else who’s been caught up in the hustle culture. 

She’s now a huge advocate for better work-life balance and mental health, and she founded Thrive Global to help others avoid the mistakes she made. Pretty inspiring, right?

What Steps Should You Take To Keep Your Mental Health Sound?

You wouldn’t neglect the health of your business, so why would you neglect your own? 

Here are a few steps you must take before things go south and you lose your peace.

Prioritize Self-Care: Running a business can feel like there’s always something more to do, and taking care of yourself can easily slip to the bottom of your to-do list.

But here’s the thing: if you’re not at your best, your business won’t be either.

Regular breaks, eating well, getting enough sleep — these aren’t just good habits; they’re what keep you going. So, make self-care non-negotiable. Think of it as part of your job — because it is.

Set Boundaries: We know your business is your baby, and you want to give it everything you’ve got. But even parents need some downtime (just ask any mom—they’ll tell you boundaries are everything).

So, give yourself some liberty to unplug at the end of the day. Set some boundaries. Take breaks.

That late-night email in your inbox? It’ll still be there in the morning, and you’ll handle it better after a good night’s sleep.

Get Help When You Need It:  If you’re feeling overwhelmed, it’s okay to reach out.

Talk to a therapist, join a support group, or just have a coffee with a friend who gets what you’re going through. You don’t have to carry everything on your own shoulders.

Asking for help isn’t about being weak; it’s about being smart. It shows you’re strong enough to recognize when you need a hand.

Regret #3 Overextending Financial Resources

Picture this: You’ve got a fantastic idea, and you’re ready to make it happen.

But here’s the thing — scaling a business can get expensive quickly. Suddenly, you’re juggling debt, bills are piling up, and the financial stress starts creeping into everything you do.

We get you. It’s easy to get caught up in the excitement of growing your business. You want to move quickly, grab the best tools, and hire top talent, and sometimes it feels like the only way forward is to keep spending.

However, overspending without careful financial planning can lead to significant challenges, often pushing businesses to the brink.

In addition, there’s that time and situation when the numbers just don’t add up, and you realize you might have bitten off more than you can chew.

Most entrepreneurs would agree to overspending in the name of scaling.

Take Jawbone, for example. They were pioneers in wearable tech, with products that people loved. But they expanded too quickly, invested heavily in new developments, and didn’t get the returns they needed.

Eventually, the financial strain became too much, and despite their early success, they couldn’t keep up and went bankrupt. 

How Do You Sort This Common Challenge?

Create a Financial Roadmap: Before you start spending, sit down and map out a clear financial plan.

Where’s the money coming from, and where’s it going? Make sure you’ve got a budget that covers all the basics and includes a little extra for those unexpected bumps in the road.

Hire a bookkeeper who can track every little expense for you, even those coffee mugs in your cafeteria.

Keep an Eye on Cash Flow: Cash flow is the lifeblood of your business. Regularly check your financials to make sure you’re not losing money. If something’s off, tackle it right away. The sooner you catch a problem, the easier it is to fix.

Invest Wisely: It’s tempting to throw money at every opportunity, but trust us, sometimes holding back is the smarter move.

Focus on investments that will give you the best return. Be very picky here. And don’t be afraid to say no to something that’s outside your budget, even if it seems like an outstanding opportunity.

And that brings us to another common regret…

Regret#4 Failing to Adapt to Market Changes

Remember Blockbuster? They were everywhere, and then, suddenly, they weren’t. 

Why? Because they didn’t adapt to market changes and trends. 

As an entrepreneur, you might be tempted to stick with what’s comfortable. But markets change, technology evolves, and customer preferences shift. The regret of not adapting quickly enough is painful. 

Blockbuster’s story is a perfect example of what happens when you don’t keep up with the times.

They had the opportunity to buy Netflix early on but passed on it because they didn’t see the potential in streaming.

They were so committed to their brick-and-mortar business model that they didn’t notice the world was moving online. And by the time they did, it was too late.

The market had changed, and they hadn’t changed with it.

What Should You Do About Growing Market Changes?

Being adaptable means you’re always ready to evolve, no matter what the market throws at you. Here’s what you should do to remain perennial. 

Stay Curious: Keep an ear to the ground. What’s happening in your industry?

What are your customers asking for? What’s the competition doing? Being curious keeps you ahead of the curve, so you can pivot before it’s too late.

Embrace Change: Change is hard, but it’s inevitable. Instead of resisting it, look for ways to embrace it. Whether it’s adopting new technology, trying out a different business model, or just being open to new ideas, flexibility is key.

Listen to Your Customers: They’re the ones who drive your business. Pay attention to their needs and wants.

If they’re shifting in a new direction, you should be too. Regular feedback from them can be your armor to stay relevant.

Unclear about what you need to do to start a US company? Check out our formation services. 

Regret #5 Neglecting Relationships

Entrepreneurship can be all-consuming. You’ve got a business to run, problems to solve, and a million things demanding your attention. Of course, you signed up for all of it when you let your passion drive your dreams. 

But here’s the thing: in this entrepreneurial hustle, it’s easy to let relationships slide.

Whether it’s with your family, your friends, or even your business partners, those connections can start to fray if you’re not careful.  You don’t realize what you’ve lost until it’s too late. 

Elon Musk has been open about this struggle.

He’s a guy who’s achieved incredible things, but it’s come at a cost. He has spoken openly about the impact that his work has had on his personal life, including his relationships and the toll it has taken on him.

In various interviews and biographies, Musk has acknowledged the challenges of balancing his intense work schedule with his personal life.

He has admitted that his work habits have contributed to strained relationships and multiple divorces.

For example, in a 2010 interview with Business Insider, Musk discussed the difficulties of maintaining relationships while being so deeply committed to his work.

Additionally, in the biography Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee Vance, Musk is quoted as saying that his work often took precedence over personal relationships, which had significant consequences.

How Not to Let Work Take A Toll On Your Relationship?

Relationships hold you tight when you are failing. So you must try your best to protect them at any costs. 

Take small steps but start somewhere. 

Make Time for the People Who Matter: On the surface, it sounds simple — just spend time with the people you care about. But in the chaos of running a business, it’s anything but simple.

The work stuff has a way of taking over, pushing those meaningful moments to the back burner. That’s why it’s so important to be intentional about it. 

Schedule that dinner with family, grab coffee with a friend, or catch up with a mentor. These connections are what keep you grounded and supported, even when things get hectic.

Be Present: When you’re with someone, really be with them. Put the phone down, close the laptop, and focus on the conversation. It’s amazing how much more connected you’ll feel when you’re truly present.

Remember, letting others in isn’t a sign of weakness; it’s how we get through the tough stuff together. So, lean on your people — they’re there for a reason.

Regret #6 Overlooking Personal Growth

You’ve probably heard the saying, “You can’t pour from an empty cup.” It’s never been more true than in today’s chaotic world. When you’re busy running a business, it’s so easy to forget about the person behind the scenes — you.

But keep this in mind: when you stop growing, so does your business.

The regret of not investing in yourself, not continuing to learn, and not taking the time to evolve can be a heavy burden to carry. Because, at the end of the day, your business is a reflection of you.

Richard Branson, founder of the Virgin Group, is a great example of someone who never forgot to invest in himself. 

He’s all about personal growth, constantly seeking out new challenges and learning opportunities.

Whether it’s kite surfing or ballooning, Branson is always pushing his boundaries. But it’s not just about adrenaline-fueled adventures — he also makes time for reflection, stays physically active, and gives back to society through mentoring and philanthropy. 

His commitment to personal development is a big part of why he’s been so successful in so many different ventures.

How Can You Protect Your Personal Growth?

Be a Lifelong Learner: Never stop learning — it’s as simple as that. Whether you’re diving into a new book, taking a course, or attending a workshop, every bit of knowledge you pick up helps you grow. And when you grow, your business benefits too.

But here’s the thing: learning doesn’t always have to be about business. Personal growth matters just as much. 

So, go ahead and explore that hobby you’ve been curious about or take a class that’s purely for fun. The more well-rounded you are, the more you bring to the table in every part of your life.

Set Personal Goals: Just like you set goals for your business, set some for yourself. What do you want to achieve outside of work? What new skills do you want to develop? Having personal goals keeps you motivated and inspired.

Reflect and Reassess: Every now and then, hit pause and really think about where you are on your journey.

Are you where you hoped to be—both in your personal life and in your career? If the answer is “not quite,” that’s completely okay. But it’s also a sign that something in your life needs to change. 

Regularly checking in with yourself helps you stay on track with what really matters to you. 

It’s about making sure your actions line up with your values and goals, so you’re not just moving forward, but moving forward in the right direction.

Don’t Let Regrets Weigh You Down — Let’s Turn Them into Opportunities With doola

If you’ve ever talked to someone who’s been through the rollercoaster of running a business, they’ll probably tell you this: their biggest regrets aren’t about the mistakes they made.

It’s the chances they didn’t take, the ideas they didn’t chase, and the dreams they let slip through their fingers.

We rarely regret trying, even when things don’t go as planned. But we do regret the things we keep putting off. Don’t you agree?

So, what’s that one thing you’ve been thinking about but haven’t acted on? Telling yourself, “Maybe someday”? 

Why not make today that “someday”? Because, honestly, there’s no good sense in waiting, especially when today could be the start of something amazing.

Whether you’re just starting to sketch out your business plan or you’re already knee-deep in building your dream, there’s still time to avoid these common regrets.

This journey you’re on — it’s a rare opportunity and you’ve got one shot to make it count. So, make sure you’re getting the most out of it, not just for your business’s success, but for your own sense of fulfillment. 

And here’s where doola can make a difference. 

We get it — running a business means juggling a million things at once. The logistics — like forming your business, managing finances, or dealing with taxes — can sometimes feel like they’re pulling you away from what really matters.

That’s why we’re here, to help you manage those details so you can keep your eyes on the bigger picture.

We’ve helped entrepreneurs from over 175 countries build their dream businesses in the U.S., and we’re ready to help you too. Here’s how:

Registered Agent Services: We take care of all your compliance needs, from receiving legal documents to keeping you on track with deadlines, so you can focus on growing your business.

Business Formation: Ready to form your LLC? We’ll make it simple, handling all the paperwork and helping you set up a business bank account so you’re ready to hit the ground running.

Bookkeeping and Tax Services: Let us take the stress out of finances. We’ll handle your bookkeeping and help you navigate the complexities of business taxes, keeping you compliant and worry-free.

Transparent and Affordable Pricing: No hidden fees — just straightforward pricing that lets you plan your budget with confidence.

Proven Track Record: We’ve earned a strong reputation for reliability and quality. Our clients trust us to help them achieve their business goals, and we’d love to help you do the same.

Remember, the choices you make today can shape your tomorrow. Don’t let the fear of what might go wrong keep you from taking that next step.

Sit down, think it through, and know that we’re here to help you every step of the way — turning potential regrets into opportunities for growth and success.

So, are you ready to take that next step? Book a free consultation with us today, and let’s make your “someday” happen now.