Are you lying awake at night wondering if you have what it takes to start your own business? Maybe you're already a few months in and feeling completely overwhelmed by everything you don't know? Or perhaps you're that seasoned business owner who's been grinding for years but can't shake the feeling that there has to be a better way?
I'm guessing at least one of these scenarios sounds familiar. Every successful business owner has stood exactly where you are right now: confused, uncertain, and probably making it up as they go along.
In 2003, I accidentally started an accounting practice that’s grown into a thriving firm. Through the years, I’ve learned that the most important lessons are the ones no one teaches you. And while I can't go back and fix my mistakes, I can share the hard-earned lessons that could save you years of headaches, sleepless nights, and expensive learning experiences.
By the end of this article, you'll understand the seven critical lessons that separate business owners who thrive from those who just survive...and the tips I'd give my younger self if I could do it all over again.
How I Accidentally Started a Business
I never intended to become a business owner. In December 2003, I was unemployed, collecting severance, and actively looking for my next accounting job. Then a friend asked me to do their tax return. "Sure," I said, "I can help with that."
A few days later, while renewing my CPA license at a Pak Mail franchise, the owner mentioned he'd just moved to town and needed an accountant. Within 30 days, that casual conversation turned into 20 clients. Forty-five days in, I landed my first major client—a company dealing with embezzlement issues that became 60% of my first-year revenue.
The big lesson? Sometimes the best business opportunities come when you're not actively looking for them. But more importantly, once you recognize the opportunity, you have to be willing to jump in with both feet.
Lesson #1: You Can't Do Everything Yourself (And You Shouldn't Try)
From day one, I knew I couldn't handle all the work myself. The math was simple: There weren't enough hours in the day to serve all my clients and still have time to grow the business.
So, I immediately started using what I call "boom riders"—former colleagues who could help with tax returns during busy season. I also hired administrative help and taught basic bookkeeping skills to people willing to learn.
Many new business owners fall into the trap of thinking they have to do everything themselves to maintain quality or save money. The reality is that trying to do everything yourself is the fastest way to kill your growth and burn yourself out.
Quick tip: Start delegating early, even if it means hiring people who need training. Yes, it costs money upfront, but it gives you the bandwidth to focus on growing your business instead of just maintaining it.
Lesson #2: Define What You Sell (Before You Say Yes to Everything)
For the first few years, if someone asked me to do anything that sounded like accounting, I said yes. Tax returns, bookkeeping, business consulting, forensic accounting—you name it, I did it.
This approach helped me learn quickly and build a diverse skill set, but it also created major problems:
- I couldn't create repeatable systems.
- I couldn't train staff effectively because every project was different.
- I couldn't scale because everything required my personal attention.
Saying yes to everything feels like you're maximizing opportunities, but you're actually limiting your ability to grow.
Quick tip: Define your "box" much earlier. I needed to decide what I would and wouldn't do. This would have allowed me to build better systems, hire more effectively, and create a business that could run without me being involved in every single project.
Lesson #3: Hire Help Earlier Than You Think You Can Afford It
One of my biggest regrets is waiting too long to hire the right people. For the first three or four years, I was constantly playing catch-up, working nights and weekends, and feeling like I was always behind.
My first hire was actually my mother-in-law, who needed part-time work while starting her own travel agency. It wasn't a perfect fit, but it gave me administrative support that freed up my time for higher-value activities.
The mistake most business owners make is to wait until they can "afford" to hire help. But if you're drowning in work, you can't afford NOT to hire help.
Quick tip: Hire people before you think you need them. Yes, it may hurt financially in the short term, but it will position you for growth in the long term. The cost of hiring too late is much higher than the cost of hiring too early.
Lesson #4: Don't Be Afraid to Ask "Stupid" Questions
Running a business means constantly encountering situations you've never dealt with before. In my case, I had to learn everything from getting a business license to understanding how owner distributions work.
Some of the "stupid" questions I had to ask:
- How do I get money out of my business?
- Do I need a W-2 if I'm the owner?
- What's the difference between a draw and a distribution?
I discovered that the questions you think are stupid are usually the questions everyone else has too. And the people you're asking have heard them all before.
Quick tip: Realize that success depends on your willingness to admit what you don't know and find people who can teach you. Ego is expensive in business. Don't let it cost you opportunities or lead to costly mistakes.
Lesson #5: Building a Business vs. Being Self-Employed Are Two Different Things
About three years in, I had a revelation: I could either be an accountant who owned a practice, or I could be a business owner who happened to be in the accounting profession. These are completely different approaches with completely different outcomes.
Being self-employed means:
- You are the business.
- Your income is directly tied to your hours.
- Taking time off means losing money.
- You can't scale beyond your personal capacity.
Building a business means:
- The business can run without you.
- Your income comes from systems and other people's work.
- You can take time off without everything falling apart.
- You can scale by adding people and processes.
Quick tip: Instead of hiring people to help you do your work, start hiring people to do the work so you can focus on building the business. This change in perspective is priceless.
Lesson #6: Surround Yourself with the Right Advisors
Starting a business means making decisions about things you've never encountered before. You need experts in your corner who can guide you through unfamiliar territory.
The essential advisory team for any small business:
- A good accountant (who understands your industry)
- A reliable attorney
- A knowledgeable insurance agent
- A helpful banker
But don't stop there. Some of my best advice came from other business owners who were a few steps ahead of me. They could share real-world experience about challenges I was facing and strategies that actually worked.
Quick tip: Don't be afraid to reach out to successful business owners in your area. Most are willing to share their experiences and offer advice, especially if you're not a direct competitor.
Lesson #7: Accept That A Business Never Really Turns Off
This is probably the hardest lesson for new business owners to understand, but owning a business means it never really turns off. Even 20 years in, I was up late last night dealing with a situation that required my attention.
If you're expecting business ownership to give you more free time or less stress, you may be in for a rude awakening. My kids joke that there are five seasons, not four, because tax season was a time when they basically didn't see me for months.
You need to go into business ownership with realistic expectations. The flexibility and control are real benefits, but they come with the responsibility of always being "on call" for your business.
Quick tip: While it never turns off, building something meaningful and having control over your destiny makes the sacrifice worthwhile for many people.
Ready to Build a Business That Thrives?
Starting and growing a business is one of the most rewarding (and challenging) things you’ll ever do. The lessons I’ve shared here come from years of trial, error, and hard-earned experience. If you take just one thing away, let it be this: You don’t have to figure it all out alone.
Every business owner has felt overwhelmed, uncertain, and completely out of their depth at some point. The most successful business owners ask questions, lean on trusted advisors, and focus their time where it matters most. You can do the same.
If you’re ready to take the next step, we’ve put together a free guide that dives deeper into the essential steps you need to take when starting your business.
These 10 ideas can help you avoid costly mistakes, stay focused, and build a business that works for you, not the other way around. Check it out here: 10 Essential Steps to Successfully Launch Your Small Business.
You don’t have to do it the hard way. Let’s build something great…together.
