15 Things I’d Do Differently If I Was Starting Over in Business

Business, Creative Business, Online Business, Productivity, Start Your Side Hustle | 0 comments

Introduction

If I could sit down with my just-getting-started self—the one with the big dreams, the DIY logo, and the to-do list full of question marks, I wouldn’t change the dream. But I would change how I chased it.

What I would do

Because starting a business is messy. It’s brave and beautiful and chaotic and full of lessons that don’t hit until year two or three. Or five.

So here’s what I’d do differently if I were starting over. No shame. No regrets. Just clarity, calm, and the kind of confidence that only comes from experience.

If you’re in your beginning? These are for you.


1. I’d Start Before I Felt Ready

Waiting to feel “ready” kept me stuck way longer than necessary. I told myself I needed more time, more skills, more clarity—when really, I just needed to begin.

Start where you are. You’ll grow into the next version of yourself by doing, not by planning forever.


2. I’d Focus on One Thing at a Time

Early on, I tried to do everything: blog, podcast, coach, design, post daily, build an email list. It was chaos.

Pick one offer. One audience. One platform. Build depth before you try to build everything.


3. I’d Raise My Prices Sooner

I undercharged because I was scared no one would pay. But undercharging doesn’t just hurt your income—it hurts your confidence and your clients’ results.

Price based on value, not fear. You can always raise them again later, but start stronger than you think.


4. I’d Create Systems Early

For too long, I was winging it with every email, invoice, and launch. It worked, until it didn’t.

Systems don’t have to be complicated. A good template, a saved email, or a Google Doc process can save you hours (and your sanity).


5. I’d Worry Less About What Other People Thought

I held back ideas because I didn’t want to look silly or salesy. Meanwhile, the people I was worried about weren’t even paying attention.

Most people are too busy thinking about themselves to judge you. Let them scroll, you’re building something.


6. I’d Show My Face Sooner

I spent months hiding behind graphics and logos. But people don’t connect with branding. They connect with you.

Put your face in your Stories. Say your name. Let people get to know the human behind the business. That’s what builds trust.


7. I’d Build an Email List From Day One

Social media is great for discovery, but it’s rented land. My email list? That’s mine. And I wish I’d started nurturing it way earlier.

Even if it’s tiny, start now. Send one helpful thing a week. It adds up and turns followers into clients.


8. I’d Stop Comparing My Beginning to Other People’s Middle

Comparison is a creativity killer. I wasted time feeling behind when I was actually doing just fine.

Unfollow anyone who makes you feel less-than. Your path is yours. Stay on it.


9. I’d Ask for Help Sooner

I thought I had to do it all alone to “earn it.” But community, coaching, and even hiring a VA changed everything.

You don’t have to be an expert at everything. Ask questions. Hire help. It’s not weakness, it’s wisdom.


10. I’d Document the Journey

I only started sharing openly once I had “results.” But the messy, early days? That’s the content that really connects.

People love watching someone build in real time. Share your process. Let people root for you.


11. I’d Invest Sooner (Even When It Felt Scary)

I clung to free tools and DIY everything for way too long. And while bootstrapping has its place, some investments would’ve saved me months of stress and burnout.

Spending money in your business isn’t wasteful, it’s strategic. Tools, mentorship, education, and time-saving systems pay off way faster than we think.


12. I’d Define Success My Way

In the beginning, I chased what I thought “success” was supposed to look like: six figures, client waitlists, perfect productivity. I didn’t stop to ask what I actually wanted.

Build your business around your version of success. More freedom? Less stress? Creative joy? Let that be the goal, not someone else’s revenue screenshot.


13. I’d Create More White Space

I thought being busy meant I was being productive. But constant hustle made me reactive, tired, and disconnected from the bigger picture.

Your best ideas come when you slow down. Build in breaks. Take real days off. Make space for thinking, dreaming, and breathing.


14. I’d Celebrate the Small Wins More

I used to skip over the milestones—my first client, my first Stripe notification—because I was always chasing the next thing. Looking back, those tiny moments were everything.

Celebrate all of it. The scary DM you sent. The idea you posted. The client who said yes. These are the breadcrumbs of a beautiful business journey.


15. I’d Trust Myself Sooner

There were so many moments when I second-guessed my gut. When I looked for permission instead of just moving. The truth? My instincts were right more often than not.

You know more than you think you do. You’re more capable than you feel. Trust that voice that whispers, “this could work.”


🪞 Final Thoughts: Start From Here

Would I do things differently if I was starting over? Absolutely. But every misstep gave me what I really needed: wisdom, resilience, and a whole lot of clarity.

If you’re in your beginning, here’s what I want you to know:

  • You don’t have to do it perfectly. You just have to keep going.
  • Your dream deserves patience, boundaries, and support.
  • You’re allowed to pivot, slow down, charge more, and change your mind.

And if you’ve already started? You’re still allowed to shift. Start over. Re-choose. Refine.

We don’t just build businesses, we become better versions of ourselves in the process. And that’s the real win.

Bold Leap

Creative Business, Typeface Lover

Helping you design, create, and grow your boldest ideas with actionable articles and creative inspiration.

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