There’s a lot to love about working for yourself: setting your own schedule, building something that’s yours, and deciding exactly what kind of business you want to run. But behind the posts and flexible work hours, there are lessons every founder has to learn, usually the hard way.
We asked entrepreneurs to share what they wish someone had told them before they became self-employed. Their insights aren’t warnings, they’re the kind of wisdom that can help you start smarter.
It’s All Up to You — and That’s Empowering
One business owner admits she underestimated just how much responsibility comes with the responsibility of being self-employed.
“That everything would be up to me and if I didn’t do it, it wouldn’t get done. I know this might seem obvious and in hindsight it really is, but when I first started out, I didn’t fully comprehend that I wouldn’t have co-workers to help share the burden or pick up the slack.” -Kathryn Smith, A Way Abroad
The good news? That realization can be incredibly motivating. Once this individual embraced the fact that she was the driver of her own success, she found the focus and energy to move her business forward.
You’re Always “On”
There’s no 5 p.m. shutdown when you’re building something from scratch. Being your own boss means sometimes, there is no distinction between work time and relax time. One professional explains how the mental switch never fully flips, but that’s not necessarily a bad thing.
“While being self-employed gives you the freedom to work when you want, it also means you’re never completely off the clock. Even when you’re not working, your mind is always running through ideas, deadlines, or the next move.” -Matthias Neumayer, Branding5
When you love what you do, it’s natural for your brain to keep turning. The key is learning how to manage that energy and not shut it down, but channel it when it matters most.
Letting Go Helps You Grow
In the early days, doing it all yourself can feel like the only way. But as your business grows, so does the need to trust others. That shift was a game-changer for one business owner.
“I assumed that being engaged in every activity was the parameter of me being responsible. It actually ended up slowing down the process. After I began trusting the team and letting them own their work, the whole firm enhanced.” -Jeff Matchen, Masters Roofing
By letting his team take the lead in certain areas, Jeff unlocked a whole new level of momentum for his business and for himself. Asking for help isn’t giving up control; it’s making a space to lead others.
So what should you really expect? Growth. Not just in your business, but in yourself.
Self-Employment Is a Learning Curve
Here’s what these founders want you to keep in mind:
- You’re in charge and that’s where your power comes from
- Your brain will stay busy, but it means you care
- You can go further with others, even when the vision is yours
Self-employment isn’t perfect, but for many, it’s the most rewarding path they’ve taken. Learn as you go. Build what feels right. Trust that every challenge is part of the process!