10 Entrepreneur Lessons From 10 Years of Entrepreneurship

10 Entrepreneur Lessons From 10 Years of Entrepreneurship

I’ve been an entrepreneur for over 10 years now, and the journey is unlike anything I thought it would be. For starters, I thought I would be a billionaire by 30. I’m now 33, and let me tell you, I’m not even close. Throughout this journey, I’ve developed so much knowledge and wisdom through trial and error that it’s honestly a miracle I’m still here today.

Here are 10 years of lessons as an entrepreneur:

1. The Journey is You

Most entrepreneurs think the journey is about building their business, but in reality, it’s much more about them. As an entrepreneur, you will constantly be building, breaking, and rebuilding yourself.

You will be forced to face all of your weaknesses and work on them one by one, brick by brick. Any delusions you had about who you thought you were will be grounded in reality, and you will have to build up from there.

You will have to learn how to be a better communicator, manage yourself before you can effectively manage others, and most importantly, be accountable for your actions. Every mistake begins and ends with you, and until you can face that, you won’t grow.

The hardest thing to overcome is the need to show up every day, despite not “having to.” There won’t be any external force telling you that you have to show up. There is no one telling you to be somewhere at a certain time to do a certain thing. It’s all on you.

2. You Have to be Stupid Enough to Think You Can

If you’re reading this article, chances are you’ve realized that you have to be stupid enough to think you can accomplish the vision you have. The reason I say “stupid enough” is because if you knew how hard it was going to be and had all the facts upfront, you’d probably think it wasn’t worth it.

There will come a point, though, when you realize the journey is going to be a lot harder than you think.

When you start off, you see this mountain you have to climb, so you run up it real fast, and when you get to the top, you raise your hands victoriously. Then, you quickly end your celebration because you realize the mountain you just climbed was just a hill blocking the view of the actual mountain ahead of you. And this mountain is much bigger and much scarier than the hill you just ran up.

The difference between entrepreneurs and wantrepreneurs is that when they see this mountain, they don’t shrink from it. As you travel on your journey, you will gain more information, and with this information, the path will seem harder to you. Realize that this is just the game we play as entrepreneurs. The path is hard—who cares? There’s no turning back. We play to win, and we move forward.

3. There is a Lonely Phase

Imagine you are a bush in the Amazon rainforest, and you are getting along just fine with all the other bushes. You talk, you have fun, and you start to share with them that you have this yearning to reach toward the light, but they just don’t understand you. You try to kill that desire in you because you don’t want to be alone, but you can’t, so you accept it. Strangely, this causes you to grow, and eventually, you have less and less contact with the bushes below, until eventually, you get so tall that your voice can’t reach them, and their voices can’t reach you.

Suddenly, you find yourself alone because you see the trees above, basking in the light, and you see the bushes below, struggling in the dark, and yet, there is no one here with you. You realize you’re not quite on the level of the trees, so you continue reaching for the light.

If you’re lucky, you may find another tree that is reaching toward the light, but the company may be temporary, as you may be growing at different paces.

There is a long stretch of time where you will be reaching for the light by yourself until you reach the skyline, rooted in your truth, in the company of trees.

When you come from the bottom, this is just the nature of growth. Embrace it.

4. Self-Help Helps, a Little

Step 1 for any newbie entrepreneur is usually to grab a plethora of self-help books to figure out success and get motivated. While books are usually useful, you want to be careful who you listen to. For newbies, the average “Think and Grow Rich” book can get you going, but books like “The Secret” can mess you up for good.

Any book that pulls you away from reason and into the inexplicable and mystical to achieve your goals is a book that will rob you of your success.

Keep in mind that many of these “Get without working” books were written to sell as many copies as possible to people who want to have without doing.

Motivation is important, but you want to make sure you’re consuming things that won’t steal your fire, make you docile, or make you excuse your pitfalls as “happening for a reason.”

Use the 80/20 rule. Read 80% of books that contain useful, practical knowledge that will serve as resources to help you advance your goals, and 20% on things that get you going and ramped up. Because times will get hard, and it won’t always be easy to stay motivated.

5. Hard Work is Overrated

Hard work is one of the biggest myths when it comes to entrepreneurship. Hard work on the wrong thing will not only ensure you fail, but the harder you work, the quicker it will happen. You don’t want to put everything on effort because effort can create such intense focus that you miss opportunities because the goal becomes effort, not growth.

If you’re going to be any good at entrepreneurship, you have to be good at decision-making. However, in order to be good at decision-making, you have to take the time to rest and reflect on your efforts with a rested mind. A tired mind can’t think clearly.

Take care of your health, find time to rest, and keep in mind that more important than how much time you spend at work is what work you do within that time. A good 4 hours beats a crap 16 hours any day of the week.

Entrepreneurship isn’t even a marathon; it’s a lifelong walk.

6. Consistency Beats Effort

That being said, consistency beats effort. Figure out what activity is going to cause the most growth for you, and spend at least 1 hour doing it every day. Your wins aren’t going to come from the big thing you did for 1-2 weeks. Your wins are going to come from the little things you did every day.

In the early 20th century, explorers Roald Amundsen and Robert Falcon Scott raced to be the first to reach the South Pole. Amundsen’s team adhered to a disciplined strategy: marching 20 miles every day, regardless of conditions. This steady, consistent approach led them to victory and a safe return. In contrast, Scott’s team pushed hard on good days and waited out bad weather, resulting in exhaustion and eventual tragedy.

The “20 Mile March” is a concept that resonates deeply with the reality of entrepreneurship and business, where success is less about grand gestures and more about consistent, disciplined progress over time.

Imagine you’re on a journey, not a sprint but a marathon. The 20 Mile March is the idea that instead of exhausting yourself in short bursts, you commit to moving forward at a steady, sustainable pace—20 miles a day, no matter what. It’s about showing up with the same level of effort, whether conditions are favorable or not. Whether it’s sunny and you’re full of energy, or it’s storming and you’re exhausted, you keep moving.

In business, this translates to setting clear, achievable goals and hitting them consistently, day in and day out. It’s about maintaining focus, even when distractions tempt you to either speed up recklessly or slow down in the face of challenges. The 20 Mile March teaches us that progress isn’t about making a giant leap all at once; it’s about making steady, measurable gains over time.

This discipline doesn’t just apply to good days. It’s easy to overextend when everything’s going well, to push too hard and then burn out. But the real strength of the 20 Mile March is in its insistence on consistency, even when you feel like you could do more. This controlled pace prevents the highs and lows that can destabilize a business and keeps you moving forward steadily, building momentum without overreaching.

On the flip side, when things are tough—when resources are scarce, and the environment is hostile—sticking to your 20 Mile March means you’re not giving up. You’re not succumbing to the temptation to ease up or halt progress. Instead, you keep pushing forward, even if the progress is slower than you’d like.

This is the mindset that separates the successful from the rest. It’s not about who can go the fastest in a short sprint, but who can endure the long haul, who can maintain that relentless, steady progress no matter what. Because in the end, it’s not the biggest leaps that define success, but the consistent steps forward. That’s the power of the 20 Mile March. It’s about resilience, discipline, and the commitment to keep going, one mile at a time, every single day.

7. Hiring is Important, Delegation is a Balance

Self-employment and entrepreneurship are often used interchangeably, but they’re fundamentally different paths. If you’re aiming to be an entrepreneur, you need to master the art of hiring and delegating. However, one of the biggest pitfalls entrepreneurs fall into is the desire to delegate everything right off the bat. While delegation is crucial for scaling a business, doing it prematurely can leave you disconnected from the inner workings of your own company.

To be a successful entrepreneur, you need to strike a balance. It’s important to wear some of the hats yourself initially, not because you intend to do it all forever, but because you need to understand the essential aspects of your business. Whether it’s by speaking with experts, rolling up your sleeves and doing the work yourself, or taking the time to learn the ropes, this foundational knowledge is what will make you effective at hiring the right people later on.

When you have a solid grasp on what each department or role entails, you’re in a better position to delegate tasks to experts who can scale that aspect of your business. This approach prevents you from being the kind of entrepreneur who delegates blindly, losing touch with how your business operates. Conversely, it also keeps you from becoming the entrepreneur who tries to do everything alone, ultimately stalling growth because you’re too caught up in the day-to-day operations.

In essence, successful entrepreneurship is about balance—understanding enough to be informed, but not so much that you can’t let go. It’s about knowing when to dive in and when to step back, ensuring that you build a business that’s not only sustainable but scalable as well.

8. Data is a Broad Word

Data is a broad term, and many entrepreneurs, particularly those just starting out, struggle with how to respond to it effectively. One common mistake I see startup entrepreneurs make is running small-scale tests—maybe a hundred dollars over a week—and then thinking they’ve gathered enough data to make big decisions. The problem is, they often don’t realize they were just a bit more time or a few thousand dollars away from hitting on something truly valuable. Instead, they prematurely scrap the marketing channel they were testing, missing out on potential success.

It’s crucial to understand that what you call “data” needs to be substantial enough to guide meaningful decisions. What constitutes significant data varies from business to business, and especially in a startup environment, you can’t rely on how things have been done before or what works for others. Your journey is unique, and so too is the data that will guide you. You need to be patient and committed to gathering enough information before making any hasty moves.

On the flip side, there are also entrepreneurs who overreact to data that’s just them in a room with themselves. For instance, they’ll create a version two or three of their website before anyone has even seen version one. They’re iterating endlessly based on their own assumptions, without actually getting anything out into the market to test. They’re not gathering any real feedback or serving the market; they’re just responding to their own internal dialogue.

The key takeaway here is to ensure that you’re actually creating data by engaging with the market before you start reacting. It’s about finding that balance—being careful not to scrap something prematurely, but also not getting stuck in a loop of constant iteration without real-world input. Data should inform your decisions, but only if it’s substantial and genuinely reflective of market realities.

9. Little Hinges Swing Big Doors

“Little hinges swing big doors.” This saying holds profound truth for entrepreneurs, where the ability to make the right decisions is often more critical than sheer effort. As an entrepreneur, you must understand that success hinges on the decisions you make—whether it’s about the people you hire, the marketing channels you pursue, the industry you choose, or the products and features you offer. Even seemingly small choices, like the design of your website or the color scheme you use, can significantly impact your business’s growth and scalability.

To be a successful entrepreneur, you must be a skilled navigator and decision-maker. More importantly, you need to anticipate the future, a trait that some might mislabel as anxiety. In reality, this healthy paranoia is what keeps an entrepreneur sharp, ready to test different environments, and quick to pivot when necessary. It’s about knowing when to change course, when to improve, and when to scale up.

Effort, while important, is primarily valuable because it generates data—data that you must reflect on to make informed decisions. Entrepreneurship isn’t just about working hard; it’s about working smart. It’s about interpreting the information in front of you, anticipating potential challenges, and making decisions that will swing those big doors of opportunity open.

10. Industry and Timing

Industry is everything. The success you achieve as an entrepreneur is often more about the industry you’re in than your personal skills or how good you are at being an entrepreneur. Many don’t realize that their level of success can be heavily influenced by the industry they choose. You might be putting in a tremendous amount of effort in one industry, only to see modest returns, whereas switching to a different industry could yield exponentially greater results with half the effort.

The industry you pick determines the value you can provide and how that value is rewarded. Take Warren Buffett, for example—one of the greatest investors of all time. Yet, when he ventured into small business ownership as a gas station owner, he failed. Had he judged his worth based on that failure, he might never have gone on to become the legendary investor we know today.

As an entrepreneur, it’s crucial to evaluate whether your struggles stem from your abilities or simply from being in the wrong industry. Sometimes, the environment you’re in—the garden, so to speak—isn’t fertile enough for you to reap the rewards you’re aiming for. It’s not always about working harder or being better; sometimes, it’s about finding the right field where your efforts will bear the fruits you desire. Understanding this can make all the difference in your entrepreneurial journey.

Industry is everything, but timing is equally crucial. The success you achieve as an entrepreneur is often a combination of choosing the right industry and hitting the market at the right time. You can have the perfect idea, but if the timing is off, your chances of success diminish. Sometimes, people aren’t ready for what you’re offering, or maybe you’re too late to capitalize on a trend. Conversely, you might find yourself too early, introducing a product or service before the market is ready to embrace it.

Being a first mover isn’t always the best strategy. History shows us examples where the first to market didn’t necessarily win the race. Yahoo was a prominent search engine before Google came along, but it was Google that ultimately revolutionized the way we search the internet. Similarly, MySpace was the pioneer in social media before Facebook took over and became the dominant platform. In both cases, timing and execution played significant roles in determining who would come out on top.

As an entrepreneur, you must understand that your success is shaped not just by your industry but also by your timing within that industry. It’s about finding the right moment when your idea can thrive, and then executing it with precision. Both elements—industry and timing—work hand in hand to create the fertile ground needed for your business to grow and succeed. Recognizing this can help you navigate the entrepreneurial landscape more effectively, ensuring that you’re not just working hard, but also working smart.

Get Yourself Some Mentors

Entrepreneurship is a long game, one that requires resilience, adaptability, and a willingness to learn. You can and should learn from the entrepreneurs who came before you, and having mentors along the way is invaluable. But at the end of the day, your success will come down to you—your ability to adapt, to evolve with changing times, and to navigate the challenges that arise.

In today’s fast-paced world, where new technologies are emerging at an unprecedented rate, the stakes are higher than ever. Technology offers incredible opportunities for success, but it also raises the level of competition. Other entrepreneurs have access to these same tools, so the race is on. Moving quickly is important, but moving smartly is even more crucial. That’s where a strong network of mentors and peers comes in. Having a team of advisors—those who can offer first, second, and third opinions—can save you time and help you avoid costly mistakes. Access to a mastermind of like-minded entrepreneurs can accelerate your learning curve, allowing you to navigate the complexities of your journey more effectively.

In the end, the journey of entrepreneurship is about you. It’s about how hard you work, how smart you work, and how well you collaborate with others. But most importantly, it’s about the value you’re able to provide to the world. Adaptability is your greatest asset; you can evolve over time, or risk becoming obsolete overnight. The choice is yours, and your success will ultimately be determined by your ability to navigate this journey with wisdom, agility, and purpose.

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