5 Mistakes I've Made as a Solopreneur

We always hear about the wins on LinkedIn, but that's not the full picture. Truth? I've made plenty of mistakes in my journey as a solopreneur the past couple of years (and I continue to make them daily). From understanding pricing to figuring out my value proposition, it’s been a rollercoaster of trial, error, and growth.

Honestly, it’s been both wonderful and challenging and humbling. There have been moments of doubt but every mistake has been a lesson in disguise. So, in the spirit of sharing what I’ve learned, here are five mistakes I’ve made—and some advice to help you avoid them.

1. I Wasn’t Clear on My Niche

In the beginning, I was a generalist, thinking I could coach anyone on anything. Over time, I realized that trying to be everything to everyone wasn’t sustainable—or fulfilling. By focusing on what I’m truly passionate about (life transitions, life design and personal growth) I’ve been able to attract clients who I’m genuinely excited to work with and have a bigger impact.

Advice: Take the time to identify your niche. (And don't worry, you may only be able to do this after you've been working on your business for a bit). What problems do you most want to solve? Who will you serve? Will you work with organizations or direct with clients? The clearer you are on your value proposition, the more aligned clients you’ll attract—and the more confident you’ll feel in your work (and pricing!).

2. I Was Afraid to Say No

In my early days, I said yes to every client—even the ones I knew weren’t the best fit. Over time, I realized this was a disservice to both of us. As I became more confident in my value and clearer on my niche, it became easier to say no to clients who weren’t a good match, allowing me to focus on those I could truly help. I also did end some partnerships that weren't working out, don't be afraid to do this!

Advice: Saying no is hard, especially when you’re starting out. But trust me, it’s better for your business long-term. When you work with the right clients, you can deliver better results—and that’s ultimately what will build your reputation.

3. I Assumed Clients Would Find Me Easily

I thought referrals would come rolling in, especially given my past career success and network. While I’ve had a steady stream of clients, many came from unexpected places, like a coaching platform and LinkedIn activity. Building a business takes time, and clients don’t always just show up at your door. I've also seen a lot of seasonality in my business that I wasn't aware of.

Advice: Be intentional about your customer acquisition strategy. Whether it’s social media, referrals, or working with organizations, figure out where your leads are most likely to come from and focus your energy there. You'll have to be consistent with your efforts and really put yourself out there which may feel uncomfortable!

4. I Didn’t Set Enough Ground Rules

When I first started coaching, I was eager to please and I didn't always have the direct conversations around boundaries and expectations. The result? Some clients showed up unprepared or uncommitted or weren't able to give the time that's necessary for coaching to be successful. Coaching (and many other business partnerships) works when both parties commit and show up fully, so setting clear expectations early is key.

Advice: Have a clear agreement that outlines the partnership. Be specific about session frequency, cancellation policies, and the work that is required from the client. Check if it's the right time for them. When both parties know what’s expected, it makes everything smoother—and you’ll have stronger coaching outcomes.

5. I Struggled With The Payment Part of the Business

Coming from a corporate career where I had a regular paycheck and never had to ask for money, this was an adjustment for me. I wasn’t clear at the start about my rates or how to structure my offerings, and I sometimes wasted time chasing my clients for payments (not fun for anyone). Over time, I developed the right packages and payment setup that has reduced my stress in this area significantly.

Advice: Get clear on your offering early. Research other businesses in your niche and price accordingly. And get comfortable asking for payment upfront or set up a simple system that does it for you—save yourself the stress and awkward follow-up emails.

Final Thoughts: If you’re on a solopreneur journey, don’t be afraid of making mistakes—they’re inevitable. The key is learning from them and continuously refining your approach. What’s one mistake you’ve made in your business that taught you something valuable? Let’s share so we can help each other on this journey!

(P.S. If you’re seeing me for the first time, I’m Steph, an executive coach living in Italy. After 20 years in corporate, I started a new chapter in life and now help others design careers and lives they love. Follow me ?? for more insights on coaching, solopreneurship, and life in Italy.)