THE CONFESSION:

“Summer always seems to expose the cracks in our partnership.

My cofounder has children, I don't, so naturally our summers look quite different. I completely understand why they need more flexibility and I genuinely want them to have that time with their family.

But if I'm honest - part of me sometimes feels like I'm the one carrying more of the business while they're away… I feel guilty even thinking that.

I don't want to resent them. But I really don't know how to address it.”

Black baseball cap with a red star logo on the front.

What I'm sensing here is a theme I see a lot, and one I find people are often quite resistant to discussing: fairness.

Firstly, I relate. I'd like to think I'm beyond measuring what's fair and what isn't, but I've definitely felt it before in my own business partnership. It isn't a feeling I want to experience! But when we're under pressure, it's even more likely to crop up. The tricky bit is that fairness is completely subjective, which often makes it harder to talk about because there isn't a "right" answer.

It seems that summer has just shone a light on something that's true all year round: healthy partnerships aren't built on thinking that you'll always be able to contribute equally.

Life doesn't stop because you've started a business. Today the example might be kids. Next year it could be caring for a parent, illness, burnout, fertility treatment, or another season of life where one of you simply has less capacity. Long-lasting partnerships are built on creating enough flexibility and trust to navigate those different seasons, together.

One of the reasons many of us start businesses is for flexibility. But ironically, successful partnerships often rely on finding consistency. The challenge isn't choosing one or the other - it's designing the right structure for you, so that you can actually be flexible when life asks for it.

When I read your confession, I'm curious what you mean when you say you're "carrying more of the business." What are you actually measuring there? More time? More output? More decisions? More emotional load? More responsibility? How are you measuring contribution? It's worth sitting with that question because it helps you move from a feeling, to something more specific and practical that you can actually discuss together.

I'd also encourage you to think about the story you're telling yourself. If previous summers have felt difficult, it's easy to assume this one will be too. We can almost begin carrying the resentment before anything has actually happened - and that in itself can end up creating the exact situation we’re trying to avoid. So ask yourself: what did I / we learn from last summer that could help make this one different?

It's also worth saying that if you're reading this and you’re a co-founder who needs more flexibility this summer, you may well be carrying something too. Worrying that you might miss out on things? That you're asking too much? Concern that you're letting your co-founder or the business down? Or maybe none of those things! Everyone’s experience is their own - it’s just about sharing those concerns so they can be understood and considered.

For me, this all comes back to expectations. Most resentment doesn't come from taking holidays - it comes from the unspoken expectations around those holidays. We assume we're both working to the same expectations when we've never actually talked about them.

So before the summer gets going, create some space to design it together.

Talk about what flexibility looks like for each of you. Be realistic about what you can each contribute rather than what you'd like to contribute. Agree how you'll communicate while one of you is away, what genuinely needs responding to, what can wait, and how you'll check in once summer is in full swing.

You don't need to solve every scenario in advance. You just need to try and remove as many assumptions as possible.

Because the goal isn't for everything to feel perfectly equal - I don’t know if that can ever be the case. It's to feel like you've built a partnership that's connected and able to flex with the seasons, without it cracking your foundations.

The Pittsburgh Steelers logo, featuring a stylized oval with the word 'Steelers' and two blue four-pointed stars.

A QUESTION FOR YOU ALL TO ASK YOUR CO-FOUNDERS:

WHAT EXPECTATIONS HAVE WE NOT TALKED ABOUT FOR THIS SUMMER?

This edition was published on the 26th June 2026