“I should have done it sooner.”

It’s something that I’ve said (or thought) a lot over the years, regardless of the job I was in at the time

Different roles, different businesses, different phases of my professional life but the same five words kept on popping up.

Looking back it strikes me that it’s not the big leaps forward that I remember most vividly – it’s actually the things I didn’t do or the things I left too late.

After working with loads of founder-led growth businesses over the years, I’ve noticed the regret nearly always clusters in the same place for others too – they don’t linger on the the decisions that didn’t work out, but the decisions that got parked for too long are seared into their memories.

Things like conversations avoided, roles left unfilled or changes never quite enacted properly all probably fall into the same category .

To be honest, I’ve done plenty of these myself over the years. As an MD running a digital agency a decade or so ago, I let a struggling client relationship drag on for the best part of a year because ending it felt like the bigger risk. It wasn’t.

The regret wasn’t the ending itself – with the benefit of long term hindsight, it was the year I spent not ending it while watching the team struggle to service the client effectively.

There’s decent research behind this, albeit from wider life. When people look back on their lives, they tend to regret the things they didn’t do far more than the things they did. Inaction lingers in the long term memory.

For founders that matters because indecision rarely feels like a decision. It feels like prudence. It’s like you’re being careful and keeping your options open.

But are you really keeping your options open? I wonder if you’re paying for the delay, but you can’t see that in the moment.

Here’s the thing though: knowing all this doesn’t actually make you decide any faster. So over the years I’ve evolved a handful of ways to think about it – five things that help me (and nowadays the founders I work with) carry less of this stuff around.

1. Lean towards action. When you’re genuinely torn and the stakes are recoverable, your bias should usually be towards doing something rather than waiting. For me, a decision you can learn from beats a delay you can only regret. Most of the time the cost of being slightly wrong is far smaller than the cost of the wait – and you find that out much quicker.
2. Narrow the field before you choose. The more options you actively weigh, the more “roads not taken” you have to worry about later on. Twelve candidates, five agencies, a dozen tools that all do roughly the same thing – those are wide option fields. Sift hard to the two or three that genuinely fit, then choose from those. You’ll decide faster and you’ll second-guess yourself less afterwards.
3. Remember the other road had potholes too. When you regret a choice, you’re comparing what actually happened against an imaginary version where everything went right. It wouldn’t have but we always imagine otherwise. The founder who took the investment regrets the dilution. The one who turned it down regrets the slow grind. The grass is greener on the road you didn’t take because you never had to go along it. Be kind to yourself.
4. Bank what you got right. Even a decision that didn’t land usually taught you something worth keeping – it tightened your hiring process or showed you a market wasn’t really there before you’d bet the year on it. A decision you learnt from isn’t really a mistake. Name the thing you learnt and move on.
5. Almost nothing is a one way door. Most decision doors open both ways and you can walk back through. Reserve the genuine agonising for the small handful of calls that are genuinely hard to undo – the “bet the company” moments – and treat the rest as recoverable (albeit with some discomfort at times). Most of the decisions that keep founders up at night are everyday, reversible calls but they feel like irreversible ones because the founder got too close.

I want to add a word of caution on all this because it’s easy to take the wrong lesson from what I’m saying.

Narrowing your options is not the same as not looking properly. If you cut the field to one before you’ve actually understood the choice, you’re not really being decisive. I’d say really you’re guessing with confidence. The point was never fewer options for their own sake – it’s spending your attention on the ones that genuinely matter and then moving decisively.

And life is just complicated. You’ll get some of these wrong however carefully you think about them. That’s not a flaw in your judgement. It’s simply just the game that we all have to play. Very few single decisions change the course of your business as much as they feel like they will in the moment.

So I’m going to leave you with three questions to sit with this week:

• Which decision have you been calling “keeping my options open” that’s actually just you delaying?
• What’s the real cost of the call you’re not making – not the risk of getting it wrong but the price of the waiting game you’re playing?
• And if you knew the door opened both ways, would you walk through it today without any more dithering?

I’m always happy to chat any of this through. Decision-making is one of the most underrated skills and I love to teach and learn more about it.