Peer Support for Solopreneurs
What started as an experiment, proved to be far more successful than I expected.
“Did you notice that no one confirmed the meeting or the location today?”
Neil looked at Ranti, Freddie, and me as we were wrapping up our last Business of Coaching meeting at Victoria. We never met at this co-working space before, and we had arranged the time and place to meet weeks in advance. Someone’s plans might have changed. But no one thought to double-check if the meeting was going ahead because by this point we just trusted each other to show up.
It all started a year ago. I whatsapped a few coaches I knew asking who would be up for forming a small “business of coaching” group to meet on a monthly basis and talk business. I wanted to share lessons and hold each other accountable.
A few people said yes, so we formed a group and contracted for one year. Our group meets monthly for two hours, on zoom or in person, sharing bi-weekly written reflections on how our coaching business is doing: customer acquisition process, sales numbers, challenges and successes.
When I asked, at the end of our last 2024 meeting this week, if we’re willing to re-contract for another year, I knew we would. It was too good an opportunity to miss.
Why every solopreneur needs such a group
Nearly every coach is a solopreneur, building a business of one. However, the lessons we learned aren’t specific to coaches. Whether you’re a fractional CTO, a self-employed yoga teacher or an AI consultant working for yourself, you’ll benefit from being part of such a group. Here is why.
Perspective. Seeing other people approach the same challenges you have gives you the information to know how to steer your own business. In particular, this concerns money, the least favourite topic for anyone. It takes time to build the trust to start having open conversations about how much we’re making and why.
Emotional support. If you’re a solopreneur, it means you are the entire team. So when you feel down or confused, your entire team is feeling down and confused. The strength of real teams composed of several people is that they support each other: if one person is low on energy, the enthusiasm of their colleague will often be enough to put things back on track. As solopreneurs we create it for ourselves.
Peer accountability. We share written reflections on how our coaching business is doing on a bi-weekly basis. I know I wouldn’t be sitting down and reflecting on my numbers, goals and challenges in writing if I hadn’t promised to send my update to others.
Why our Business of Coaching group works
In hindsight, the reasons it works so well for us are simple.
Right size. I had a strong intuition that 4-5 people is the right size. I used to be part of similar groups1 of 7-8 people when I was CEO of Makers and it was too much.
If you have 8 people, you need to meet for 4 hours, which is too long, especially on zoom. Plus, someone is always on holiday or can’t make it. Aligning calendars, especially rescheduling, becomes very hard.
It’s easier to build trust among 4-5 people than 7 or 8. And trust is the most important foundation for success of such a group.
Right scope. We talk primarily about business of coaching. Even though no topic feels off-limits and personal questions come up all the time, there is a clear professional focus.
Right people. All four of us are solopreneurs with a few years of experience as full-time coaches. We’re similar enough to understand each other well, but different enough not to feel like we’re competing with each other.
Clear structure. We commit to meet monthly for 2 hours, which gives each of us 10-15 minutes to share our update and 15-20 minutes for the group to discuss. We share a written update bi-weekly (well, that’s the intention — I’m late this week myself). The update is free-form but it’s, basically, numbers (money, hours, etc) and reflections on those numbers without any client information.
Photo by Alejandro Escamilla on Unsplash
How to start your own group for 2025
If you’re a solopreneur and you aren’t part of such a group, I can’t think of a reason you shouldn’t start one right now. The investment of time and effort is absolutely worth it. Here is how:
Reflect on the size and the format you want to create. How many people? What is the goal? What process will work best? Do you give each other advice or it’s strictly advice-free? This will be a helpful starting point.
Think of the people you’d love to see there. Who are those you respect and trust enough to be vulnerable in front of them? Who will complement each other well?
Once you’ve got a list of names, pick up a phone or meet in person, one by one. Sell your vision but also get a sense if they will be as committed as you are. I made a mistake of sending a whatsapp message to a group of dozens of coaches, thinking that maybe 2-3 people will reply. Over ten expressed interest and I embarrassed myself by having to publicly pick and choose (and apologising a lot in private). Don’t be me.
Once you’ve got a group, discuss the format and the process again. There’s a balance somewhere between having a clear vision of how it will work and being open enough to modify it to make it work for everyone. The goal is to find a format that works for all of you.
Commit to a specific timeframe. In our case, we committed for one year. Still, it’s a good idea to ask from time to time what works well and what needs to be adjusted. In our case, we moved from weekly to bi-weekly written updates.
Most importantly, lead by example. A group of 4-5 people doesn’t need a formal chair, but the person who initiated it will still be perceived as responsible for it. It may be a team effort, but others won’t be more open, more vulnerable, more reliable or more generous that the person who started it.
In lieu of conclusion
The conclusions are obvious here — if you’re a solopreneur go and build your own support network, so in lieu of conclusion, here are the reasons my fellow coaches in my Business of Coaching group are awesome.
Neil MacKinnon. You should work with Neil because he brings experience from cultural and creative industries to his coaching. Long time ago he was a professional musician before transitioning into senior leadership roles in creative industries. Neil and I trained together years ago at the Academy of Executive Coaching, where he is now part of the faculty. Oh, and you should sign up to his newsletter.
Ranti Williams. You should work with Ranti because her background in investment banking and strategy consulting, combined with her coaching training and boundless energy makes her a powerful coach. Ranti is a special advisor to Meyler Campbell, a premier coaching training organisation where she trained back in the day. Here’s Ranti’s newsletter that you should subscribe to.
Freddie Birley. You should work with Freddie if… well, if you’re lucky enough find her available. She coached over 150 founders and investors and is well known within the London tech ecosystem for a good reason. Freddie offers both 1:1 coaching and workshops for VCs and accelerators.
And… 🎄🎉Merry Christmas? May the next week bring you nothing but good surprises!
If you’re part of Foundrs, they run Tribes. If you’re part of ICE, they run Cubes. If you’re part of YPO, they run Forums. All of these are groups of 7-8 entrepreneurs at a similar stage with a professionally trained chair who go through professional and personal challenges once a month. It’s very powerful if done well.