Advice for My Younger Self: 18 Insights from Entrepreneurs

To be honest, the advice I’d give my younger self is this: don’t confuse motion with progress. In my early days, I was obsessed with looking busy — running from meeting to meeting, sketching out five new ideas a week, and convincing myself that speed equaled success. But when I look back, most of that activity was just noise. The signal came the day a mentor pulled me aside and said, “If you can’t point to the one thing that truly matters this week, you’re not building a business; you’re chasing a feeling.” That line hit harder than any financial loss ever did.

What I believe is that the real inflection point in my journey came when I learned to prioritize clarity over chaos. I remember shutting my laptop one afternoon, taking a walk, and admitting to myself that half the things I was working on weren’t moving the company forward. That moment of honesty forced me to cut projects, delegate faster, and focus on the small handful of decisions that actually generated momentum.

I am very sure that younger founders underestimate how powerful disciplined focus is. If I could whisper one insight back in time, it would be this: success comes from choosing what to ignore just as much as what to pursue.

If I could give my younger self one piece of advice about starting a business, it would be this: don’t confuse slow progress with failure. Building my company taught me that the hardest part of entrepreneurship isn’t the work — it’s managing your own doubt when the results don’t show up right away.

There were stretches where I felt genuinely depressed. I remember spending months building out thousands of category pages, fixing crawl issues, and rewriting comparison logic, only to see almost no movement in traffic. It felt like shouting into the void. But two moments pulled me out of that mindset.

The first was the day I finally saw a major SaaS company engage with my outreach — a real backlink from real effort. It proved the system worked, even if slowly. The second was noticing how the site’s architecture and quality had a quietly compounding power; things I built months earlier suddenly clicked into place and drove opportunities I couldn’t have predicted. Those tiny wins mattered more than I realized at the time.

The lesson I wish I’d learned earlier is simple:

Breakthroughs rarely feel like breakthroughs when you’re living them — they show up disguised as small, boring wins.

If you stick through the slow parts and give compounding effort a chance to work, the business eventually reflects the persistence you put into it.

When I was in high school, my mother used to ask me what I wanted to do with my life and who I wanted to become. My answer was always: “I just want to own my own business.” I wasn’t sure at the time what type of business I wanted to own; I just knew that being an employee wasn’t for me, and neither was school. This drove my mother crazy because she knew that owning a business requires education, too. She tried diligently to get me to take a business course at the local college. This was not appealing to me whatsoever. I brushed off every attempt she made, and in the end I won the battle. But later in life, I learned that the battle shouldn’t have been fought in the first place; she was right. I made many attempts to start my own business, beginning when I was only 16 years old. I tried mobile small engine repair, importing Chinese products to resell, water garden installations, a cleaning service, and eventually a website development business. All of them had no business plan; I just threw a hundred bucks at advertising to see where it went. Most of the time, it went absolutely nowhere, or the results were weak at best. I remember a customer asking me how much he owed me for fixing his snowblower in the middle of a snowstorm. My answer was: “Whatever you feel is fair.” He gave me $20 for what I now know is a $200 job. By the time I got into the cleaning service business, I had learned that I needed set prices and not to let customers tell me how much they would pay me. The cleaning business was a little more successful.

Over the course of many years, I realized that the education I was getting in how to run a business came from making mistakes. This type of education is just as expensive as college, but it takes decades to learn this way.

Unfortunately, I passed my method of learning down to my kids. Now they, too, are learning the hard way. I often remind them that, “Education isn’t free. It doesn’t matter how you get it; it will always cost you, either way.”

After four decades, I am finally a cum laude graduate of the School of Hard Knocks. I have finally learned what it takes to be successful. I now own a successful and growing security company.

Looking back at my life, I wish I had listened to my mother. I wish I had listened to reason and hadn’t been so stuck in my stubborn ways. But since I am where I am, I feel I learned in such a way that I will never forget my lessons; I just regret the pain and stress I put myself through.

One piece of advice I’d give my younger self is this: trust the process, but build the systems early.

When I first started my pet care business, I poured everything into the hands-on work — grooming, training sessions, enrichment activities, building bonds with every dog who walked through the door. While that passion is still the heart of what I do, I wish I had understood sooner that strong systems and structure are what allow that passion to scale without burning myself out.

Clear processes for client communication, scheduling, safety protocols, staff training, and documentation of a dog’s behavior at each visit are what give you consistency and allow you to grow without compromising the quality of care. They free you to focus on what you do best: nurturing dogs, guiding owners, and creating a truly personal experience.

I’d remind my younger self that building a business isn’t just about working hard — it’s about working intentionally. Create the foundation early, let systems carry the weight, and you’ll have the space to grow, innovate, and enjoy the journey far more.

If I could hand one note to my younger self before she opened her laptop, it would say: Choose one sentence to stand on, and plan your repair before you launch.

The thing is, I spent years trying to be everything “communication” — mistaking effort for clarity and perfection for safety. The day I wrote five words — “repair before results” — my work got simpler, my offers got smaller, and my courage got bigger.

Decide what you promise, ship the tiniest version, and prewrite what you’ll do when it wobbles: who you’ll call, what you’ll change first, when you’ll try again tomorrow. Then keep your word to yourself and to your calendar.

I’d also tell her that her nervous system is a business asset, not an obstacle. Protect two real focus blocks, one urgent lane with a response window, and a hard stop at night so you can love your life while you build it.

No one hires you for your burnout — they hire you for your steadiness. The clients who stay won’t remember how glossy your first website looked; they’ll remember that, when something went wrong, you repaired it fast and were kind. That’s the kind of success worth growing into.

For many years, I believed that the more clients and projects you have, the more you grow as a business. However, I have come to realize that to achieve sustainable growth, you must first build your “business machine” with clearly defined processes. Make sure you have the “right people” in the “right roles” and the discipline to turn down any opportunities that do not align with your business vision. Looking back, I wish I had spent more time at the beginning defining what type of business I wanted to create, what value we would provide, and who our best clients were, and then had continued to protect that focus. You can generate revenue quickly, but it takes years to build a business’s reputation, culture, and trust. If I were to start again, the first thing I would ask myself before making a major decision would be, “Does this decision support the type of business I want to be running in 10 years?” Seeing things through a long-term lens will change everything.

We all deal with adversity. How we overcome it can define us.

The one piece of advice I would give my younger self about starting and running a business is to expect adversity and setbacks along the way. If you’re not prepared, they can affect you so deeply that you could lose your business.

Don’t let this happen to you. Prepare yourself ahead of time for challenges that might occur. Most importantly, prepare yourself mentally to overcome these obstacles so that you can remain calm and take them on without panicking.

So how can you prepare yourself for adversity and learn to become resilient?

You can do this by finding a mentor to advise you and help you navigate whatever challenges might occur. It’s even worth paying for mentorship because it will save you so much time in learning that it will be more than worth the cost. You can find a mentor through the Small Business Administration or by networking locally in your town.

Being an entrepreneur means being able to withstand setbacks and stay on an even keel no matter what happens. Everything will go wrong, so you should expect that. Read stories of other entrepreneurs who came back from adversity and learned how to become resilient. Resilience is absolutely necessary for every entrepreneur.

My journey involved coming back from the brink of blindness, near-bankruptcy, and a host of other challenges, all at once. It taught me that the “impossible” is achievable. My unlikely recovery is what inspired me to share my story with the world in order to inspire others.

The advice I’d give my younger self is this: structure beats enthusiasm.

When I founded my company in 2003, I had a passion for Lean and a belief that helping organizations improve was meaningful work. What I didn’t fully appreciate was how critical it is to distill complex methodologies into simple, repeatable frameworks. It took years to arrive at our three-part structure: Projects, Continuous Improvement, and Program Management. If I could go back, I’d tell myself to focus earlier on creating that clarity. Clients don’t buy complexity; they buy confidence that you can help them succeed. When you can explain your approach simply, you attract better clients, deliver faster results, and build a sustainable business rather than constantly reinventing your pitch. Beyond complexity, having a program is a competitive advantage. Clients don’t want to hear that everything can be customized. They want to hear that you have figured this out.

The second insight I wish I’d embraced earlier is to be an early adopter of how you deliver, not just what you deliver. We eventually became pioneers in 24/7 online and hybrid learning while competitors stayed stuck with stale PowerPoint presentations on Zoom calls. That forward-thinking approach differentiated us and expanded our reach. But I could have moved faster. Too many entrepreneurs cling to familiar delivery methods because those methods are comfortable, even when the market is shifting. The content matters, but how people access it matters just as much.

Finally, I’d tell my younger self to build for sustainability, not growth for its own sake. We’ve intentionally stayed lean with a small team, strategic partnerships, and steady revenue. That has allowed us to maintain quality, stay honest with clients, and weather challenges like recent retirements without a crisis. Not every business needs to scale aggressively. Sometimes the smartest entrepreneurial move is to build something that lasts, delivers consistent value, and doesn’t require you to compromise your principles to keep the lights on.

I would tell my younger self to stop waiting to feel ready before charging premium rates. In fact, I should have doubled my pricing earlier and lost sleep figuring it out later. Clients do not value your services more because you price them low; they trust what feels like confidence. When I finally quoted $6,500 for a site audit for which I used to charge $800, I got: “Sounds good. Can you send an invoice tonight?” That shook me. The deliverables were the same. The tools were the same. The price was different. Suddenly, I had more budget, less scope creep, and no second-guessing from the buyer.

All that is to say, your price is not a math problem; it is a mirror. If you undervalue your work, others will too — and they will act like it. Most early businesses do not fail for lack of effort; they fail because of weak positioning and paper-thin margins. The more you charge, the more room you have to fix, flex, or fail forward. To be clear, no one regrets charging too much; they regret how long they waited.