March 20, 2025
If you’re an entrepreneur who has survived in business long enough, you’ve likely had to solve dozens of problems without a clear and easy answer:
- How do I grow sales?
- How do I increase my profits?
- My customers aren’t buying enough, how do I keep them coming back?
And on and on it goes.
I started my entrepreneurial journey when I was 17 and was first faced with the problem of creating something new that hadn’t existed before.
From 2011 to the start of 2025, that business and those problems were my life.
As a founder and the head of marketing, it was my job to grow the business, retain the customers, and dive into the data to find problems and solutions.
The Entrepreneur’s Challenge
When you’re working inside a business, it can be difficult to step back and get a full view of what’s wrong and what the problem truly is.
One of the biggest lessons my brother taught me early on was,
“No one cares about your success more than you do.”
There is no one waiting for you to fail so they can help you out.
No one will ever push you to succeed or do the work for you.
As an entrepreneur, it’s your job to learn how to solve problems that no one else can solve or will solve (and get paid for doing it).
Navigating Business Currents
Entrepreneurship is difficult for everyone.
When you’re in the boat and only worried about progress, the idea of solving problems becomes so ingrained into every fiber of your being.
This focus makes it hard to take a step back and see where you’re heading.
Are you rowing upstream?
Is the wind at your back or blasting in your face, watering your eyes and blurring your vision?
Resistance training is the best way to strengthen your muscles.
If you want to become a stronger rower, rowing against the wind and against the current is the best way to improve.
But at the end of the day, it’s not going to take you anywhere.
While you’re struggling to row against the current, others who are weaker than you are going far further with far less effort.
When you notice this, it’s easy to get jealous (and burnt out).
So, I wanted to share some of the lessons I’ve learned over the years so you can use them to your advantage.
Lesson 1: Resistance builds strength
Business is a sport, and there’s no gym to practice in.
Doing the hard things every day and finding unique ways to solve your problems make you stronger.
Solving harder problems makes you better.
And over time, your learnings compound, and you’ll gain an edge over your competition.
Going the wrong direction isn’t a bad thing.
If you see each struggle as a reason to throw in the towel, you’ll never make any progress.
Which leads me to my next lesson.
Lesson 2: Quitting Early Won’t Make You Stronger
Each problem you solve is an opportunity to learn and grow.
Those lessons are applicable to future business or future jobs.
You may need to come up with and implement a dozen solutions to a problem before you find the one that actually works.
Failing at solving a problem is a good thing.
As Edison said,
“I have not failed. I’ve just found 10,000 ways that won’t work.”
Finding what doesn’t work is just as important as finding what does.
If you didn’t try those things, you wouldn’t have learned how to solve the problem in the first place.
In most cases, the first solution won’t work.
Trying to create new solutions and the act of implementing them is one of the best things you can do as an entrepreneur.
It will make you a better manager and a better leader.
Lesson 3: Strength is a Superpower
If you’ve been going to the gym 4x per week for 5 years, you’ll be in a lot better shape than someone who’s been going to the gym 4x per week for the past 5 months.
Comparing the weight you lift to where you started, you won’t believe how much easier it is to lift.
The same goes in business. After enough struggles, you may decide to leave your business.
Then you can start something new in a market where you feel a nice breeze at your back, rather than rowing upstream.
At that point, your strength will take you far further, far faster than anyone else in the same river who has only been there for a few months.
You can probably even jump in your boat five months later and catch up to them within a month or two if they’re not experienced.
Your knowledge, your skills, and your ability to solve difficult problems in a market that is far easier to work in is truly a superpower.
Lesson 4: Know When to Change Direction
It’s tough to give up something you’ve spent years of your life on and that is so ingrained in your identity that you wouldn’t know who you are without it.
But at a certain point, you should know that if you’ve been fighting the same problems for several years without a better understanding of what the solution is, there may not be a solution.
If you’re selling services to a newspaper and trying to grow a business helping out digital online newspapers, do you think you’ll have an easy time growing?
Would you rather be a realtor in a shrinking market or a growing market?
It’s easier to sell hot dogs to a starving crowd than to sell ice to an Eskimo.
But if you can sell ice to an Eskimo, how many more hot dogs could you sell to a starving crowd?
Persistence and determination are two of the main pillars of success as an entrepreneur. But at a certain point, if you’ve lost your faith in what you’re doing, you’ll burn out and waste your short and precious life solving impossible problems.
Conclusion
Remember, true entrepreneurial wisdom isn’t just about working harder than everyone else—it’s about recognizing when you’ve built enough strength to choose where to apply it.
The struggles you’ve faced haven’t been in vain.
They’ve equipped you with rare skills and insights that can propel you forward when you find the right current.
Don’t be afraid to pivot.
Your greatest advantage may be applying your hard-earned strength in waters where the wind is finally at your back.