Rowing Against the Current

If you’re an entrepreneur who has survived in business long enough, you’ve likely faced dozens of problems without clear or easy answers:

How do I grow sales?

How do I increase my profits?

My customers aren’t buying enough. How do I keep them coming back?

The list goes on and on.

I started my entrepreneurial journey when I was 17 and was immediately face with the challenge of creating something entirely new. From 2011 to early 2025, that business and those relentless problems became my life.

As both founder and head of marketing, it was my responsibility to grow the business, retain customers, and dive deep into data to uncover problems and solutions. When you’re working inside a business day after day, it becomes incredibly difficult to step back and gain a full view of what’s truly wrong and what the real problem is.

One of the most valuable lessons my brother taught me early on was this: “No one cares about your success more than you do.” There’s no one waiting in the wings for you to fail so they can rescue you. No one will push you to succeed or do the work for you.

As an entrepreneur, your job is to learn how to solve problems that no one else can solve or will solve, and get paid for doing it well.

Entrepreneurship is difficult for everyone. But when you’re in the thick of it, focused solely on progress with problem-solving so deeply ingrained in every fiber of your being, it becomes nearly impossible to take a step back and see where you’re actually heading.

Are you rowing upstream? Is the wind at your back, or is it blasting in your face so hard that your eyes water and your vision blurs?

Here’s where the analogy becomes crucial: 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 will absolutely improve your skills. But at the end of the day, all that effort isn’t going to take you very far.

While you’re struggling to move forward against the current, others who may be weaker than you are traveling much further with far less effort. When you notice this happening, it’s easy to get jealous and burnt out.

Over my years in business, I’ve learned some hard-won lessons that I want to share so you can use them to your advantage.

Lesson 1: Resistance Builds Strength

Business is a sport, but there’s no gym where you can practice safely. Doing the hard things every day and finding unique solutions to the problems you face is what makes you stronger as an entrepreneur. Solving increasingly difficult problems makes you better at your craft.

Over time, your learnings compound exponentially. Each challenge you overcome adds to your toolkit, giving you an edge over competitors who haven’t faced similar trials. The entrepreneur who has weathered multiple crises develops an intuition that can’t be taught in business school.

Going in the wrong direction isn’t necessarily a bad thing. If you view each struggle as a reason to throw in the towel, you’ll never make meaningful progress. The key is learning to distinguish between productive struggle and futile effort.

Lesson 2: Quitting Early Won’t Make You Stronger

Each problem you solve represents an opportunity to learn and grow. Those lessons become applicable to future businesses, future jobs, and future challenges. You may need to develop and implement a dozen different solutions before finding the one that actually works.

Failing to solve a problem initially isn’t a failure at all. As Edison famously said, “I have not failed. I’ve just found 10,000 ways that won’t work.”

Discovering what doesn’t work is just as valuable as finding what does. Without trying those unsuccessful approaches, you wouldn’t develop the problem-solving skills necessary to eventually succeed. In most cases, the first solution you attempt won’t work, and that’s perfectly normal.

The process of creating new solutions and implementing them is one of the most valuable experiences you can have as an entrepreneur. It transforms you into a better manager, a more effective leader, and a more resilient business owner.

Lesson 3: Strength Is a Superpower

Consider someone who has been going to the gym four times per week for five years compared to someone who started the same routine five months ago. The difference in strength, endurance, and capability is dramatic. When the experienced person looks back at the weights they started with, they can hardly believe how much easier those same weights feel now.

The same principle applies in business with even greater impact.

After enduring years of struggles and building your entrepreneurial strength, you may eventually decide to leave your current business and start something new. Perhaps you’ll move from a market where you’re constantly rowing upstream to one where you can feel a favorable breeze at your back.

At that point, your accumulated strength will carry you much further and much faster than anyone else in that easier market who has only been there for a few months. You could give someone new a 5-month head start, jump back into your boat, and catch up to them within a month or two simply because of your experience.

Your knowledge, your refined skills, and your ability to solve difficult problems in a market that’s far easier to navigate becomes a genuine superpower. You’re not just competing with the same tools as everyone else; you’re operating from a completely different level of capability.

Lesson 4: Know When to Change Directions

This is perhaps the most difficult lesson to internalize. It’s incredibly tough to abandon something you’ve invested years of your life in, especially when it has become so intertwined with your identity that you wouldn’t know who you are without it.

However, there comes a point when you must recognize that if you’ve been fighting the same fundamental problems for several years without gaining a clearer understanding of potential solutions, there may simply not be a viable solution.

Consider this: If you’re trying to sell services to newspapers in an industry that’s rapidly declining, do you think you’ll have an easy time growing your business? Would you rather be a realtor in a shrinking market or an expanding one?

The skills you develop solving nearly impossible problems in difficult markets become incredibly powerful when applied in more favorable conditions. The question is knowing when you’ve learned enough from the hard market to justify making the switch.

The Balance Between Persistence and Wisdom

Persistence and determination are absolutely fundamental pillars of entrepreneurial success. But there’s a crucial distinction between productive persistence and stubborn attachment to a failing strategy.

If you’ve completely lost faith in what you’re doing, you risk burning out and wasting your precious time solving problems that may be genuinely unsolvable in your current context. The art lies in recognizing when you’ve gained enough strength from the resistance to graduate to a more favorable environment.

Your struggles aren’t wasted effort if they’ve made you stronger and wiser. Every problem you’ve solved, every late night you’ve spent troubleshooting, every moment of doubt you’ve pushed through has built capabilities that will serve you wherever you go next.