One of the most challenging aspects of building With Jack is staying motivated as a solo founder. When I recognise I’m having one of those days I give myself permission to write it off.

I’ll do the bare minimum at work, go home and play video games or hit the gym. I’ll do whatever I’m in the mood to do that takes me away from work—that’s the point.

I try not beating myself up about it, but sometimes those days extend to weeks and you’re in a prolonged ‘funk’. That’s where I’ve been recently and it hasn’t been fun.

The problem with being a solo founder is that there’s nobody to drag you out of that funk.

There’s nobody to pick up the slack so you can get the rest you need to recharge your batteries.

There’s nobody to give you a pep talk to motivate you.

It’s a scary (and potentially dangerous) place to be in. When I’m in this place my productivity levels only function at, like, 25%. A few days of not accomplishing much will have me sink deeper into that funk.

I’m passionate about helping freelancers. I’ve seen the value With Jack delivers and I love what we’re building. I feel positive about its future.

All of that drives me forward, but it doesn’t mean I’m motivated 100% of the time. With this funk lasting longer than usual I evaluated what triggered it so I can avoid feeling this way in the future.


I’m working with a team of freelancers, but they’re based remotely and aren’t building With Jack full-time. This means I’m predominantly working alone. I also live alone. This is a lot of time spent in my own company. That’s fine most of the time as I function well in my own company, but recently the isolation has got to me.


This is a big one! Momentum is so important to morale, but we’ve been slow to ship updates. Whilst the business is growing (in the past 9 weeks I’ve shipped £20,000+ of insurance products), the platform itself hasn’t evolved much.

We’ve been working on a rebrand and developing the instant quote system for what feels like forever. I’ve held off on launching the new quote system until the rebrand is complete, which has slowed things down.

In June I realised waiting to ship a bunch of features as part of a big launch was a mistake, and instead I should focus on shipping smaller features on a consistent basis. This helps with momentum. However, 3 months later it’s clear I failed to take my own advice.

'Killing It' Culture

Whilst this was going on, I was looking around and seeing everyone else “killing it”. Of course, this isn’t true. Everybody is facing problems or challenges in their business, but we’re only shown the good stuff on Twitter, Facebook etc.

That’s why I’m keen to share the side of business (specifically bootstrapping as a solo founder) that isn’t glamorous. It’s also why I’m eager to follow up tweets like this:

With this:

Slow Growth

All of this was exasperated by a slow couple of weeks with sales. I’ve been spoiled by good growth lately. Since March the figures have been growing consistently, but there’s a lurking fear that it’s a fluke.

Slow weeks are inevitable for every business, but my mind instantly shifts to “my luck has run out. Time to apply for jobs”. That mindset doesn’t help with dragging me out of my funk. In fact, it puts me in an even deeper, emotional rut.

So, how did I get out of this funk? It’s important to have this conversation as it’s something we all experience. Whilst the solution is different for everyone, identifying what triggers it is a good place to start. For me, I’d say isolation and lack of momentum have been the biggest problems.

Knowing this, I started applying to business programmes to solve both these issues. These programmes would enable me to;

  • meet new people who are in ‘my world’ (business, technology, design)
  • make lasting connections. A lot of the time I hide behind my computer in Glasgow
  • feel inspired and learn new things, both of which could help with motivation
  • push myself out of my comfort zone (one of the programmes involved pitching to hundreds of people on stage in Las Vegas)

Unfortunately, all of my applications were rejected.

Enter Epicurrence

Whilst applying to the above programmes, I got a Twitter DM asking if I’d like to speak at Epicurrence—a design retreat in Yosemite. The timing couldn’t have been more perfect. I had a feeling it would be exactly what I needed, so I said yes.

  1. Meet new people
  2. Experience a new setting away from my house and office
  3. Get involved in activities away from the screen
  4. Push myself out of my comfort zone

During the day we’d go on adventures such as hiking, kayaking and mountain biking. Hiking the Mist Trail in Yosemite National Park is one of my top life experiences. As is mountain biking alone through Yosemite and coming face-to-face with a coyote.

As the sun set, we’d gather around a fire and have candid conversations about burnout, diversity and creativity. All egos were left at the door. This was about creatives connecting on a level beyond just work.

Being interviewed by Pablo at Epicurrence. Photo by Edgar Chaparro

Epicurrence was a once in a life-time opportunity, so it won’t be around to solve my next funk. However, it has reminded me of the importance of being involved in a community of like-minded individuals. Sometimes just being around others is enough to inspire creativity. This makes a huge difference to your day when you’re a solo founder.

I’ve also been feeling more motivated and we’ve locked in a date for shipping the rebrand and quote system. Spoiler: With Jack will look very different 5 weeks from now.

This experience has given me more focus and helped me refine With Jack’s direction. Community will inform the next stages of With Jack, too. But first, let’s ship that rebrand!