What if…. I had to Start Over in Business: What I’d Do Differently If I Knew Then What I Know Now

This morning, I found myself reflecting on a question many business owners ponder: If I had to start over from zero, knowing everything I know now, how would I do it? It’s an intriguing thought experiment because no two businesses are exactly alike, and while having a "plug-and-play" approach would be ideal, the reality is far more complex. Every venture comes with its own unique challenges, and external factors often shape the path forward in ways we can’t control.

Still, I wanted to share some lessons I’ve learned along the way—what I’d prioritize, change, and refine if I were starting again tomorrow. Here’s what I’d do differently:

1. Systematize Everything

I can’t stress this enough: systems are your best friend. From buying computers to onboarding employees to how prospects are greeted—everything should have a process. The sooner you organize your company around clear, repeatable systems, the better it will be for everyone. People thrive on structure—it provides a sense of comfort and reliability. A well-oiled machine is not just easier to run; it’s also more scalable.

2. Master the Fundamentals of Business Operations

Many entrepreneurs start out because they’re skilled at doing the thing—whether that’s engineering, designing, or baking. But as the business grows, you’re no longer just “doing the thing.” Suddenly, you’re managing sales, finances, HR, IT, and countless other responsibilities you might not have considered. Learning the foundational principles of business operations early on can help you navigate these roles with confidence and avoid feeling overwhelmed.

3. Hire Experts for What You Don’t Know

Owning a business is hard work—really hard work. Don’t let social media influencers fool you with tales of “easy, overnight success.” Those stories are rare, if not entirely fabricated. Most of the time, as the owner, you’re working harder and longer than anyone else. You’re “always on,” and your family might wonder where you’ve disappeared to. That’s why hiring the right people—true experts in areas where you lack knowledge—is critical. Their skills and insights will lighten your load and strengthen your business.

4. Expect the Unexpected

If there’s one guarantee in business, it’s this: things will not go smoothly. There will be highs that make you feel unstoppable, and lows where you question whether you’ll make it. Resilience is key. Prepare for the storms and celebrate the wins, but always know that challenges are part of the journey.

5. Be a Good Person—Even When It’s Hard

In business, you’ll face moments when the pressure feels unbearable, when your world feels like it’s crashing down. During those times, remember this: your employees, family, and friends didn’t sign up for the stress—you did. Don’t take it out on them. If you need to cry in a corner for a minute, do it. But when you come out, pull up your bootstraps and face the challenges head-on. Your team and your loved ones are counting on you to lead with grace and grit.

Starting from zero again wouldn’t be easy—but armed with the lessons I’ve learned, I’d approach it with a clearer mindset and better tools. For those of you on this journey right now, know that the challenges you face today are shaping you into the leader you’re meant to become.

What would you do differently if you were starting over? Let’s start a conversation—drop your thoughts in the comments below!

?