There’s a specific kind of stuck that comes with running a business. A decision lands on your desk, and you know you’re supposed to just know what to do. Trust your gut, people say. Follow your instincts. But what if your gut’s been wrong before? What if it’s led you straight past red flags you should have caught, or left you completely side-swiped by someone you trusted?
That was me for a long time. I’d been let down by people close to me, people I had good reason to trust, and it wrecked my confidence in my own judgement. Not in a dramatic, one-off way. In the way that builds up over years until you stop trusting yourself in the moments you most need to.
Here’s what changed that, and what I think most business owners are missing when it comes to making calls under pressure. It’s not about trusting your gut harder. It’s about being deliberate about whose voice is in the room when you decide, starting with your own.
The boardroom of Lisa
I had a session with a life coach a while back, working through exactly this. Why couldn’t I trust my own judgement when it really mattered? We ended up doing a visualisation exercise, going back through the times in my life I’d been majorly let down. Not in the abstract. Specifically. I found a three-year-old me in there. An eight-year-old, a 14, 26, 29 and a 35-year-old. Each one carrying a version of that same lesson, learned the hard way, at a different age.
Out of that exercise came something I still use, and I’ve started calling it the boardroom of Lisa. Whenever I’ve got a decision where I’m not sure I trust my instincts, I assemble the board. The Lisa of now takes the chair. She doesn’t push the other versions of me aside. She consults them. Gives them a voice. The 14-year-old who got badly burned by a parental figure has something worth saying about who to let in close. The 29-year-old who ignored every warning sign has a different kind of expertise: she knows exactly what getting overridden by wishful thinking looks like from the inside.
None of those younger versions of me were wrong to get hurt. They were paying attention, and they picked up something true, even if it cost them to learn it. The problem was never that I didn’t have good instincts. It’s that I’d stopped listening to the ones I’d already earned.
That’s the internal board. But there’s an external one too, and it turns out just as few people build it on purpose.
Picking your five
One of my mentors told me about her five. Five people whose opinion she asks for, specifically, when something matters. She schedules time to hold space for them, and that time is treated as more valuable than time spent with anyone else. There has to be a really good reason to pull her away from it.
I’d describe the right five as your biggest cheerleaders who are also willing to look you in the eye and call bullshit, without it costing you the friendship. That combination is rarer than it sounds. Plenty of people in your life will cheer you on. Fewer will tell you the truth when it’s inconvenient. Fewer still will do both and keep showing up afterwards.
I’ve been building my five for over a year now. The roster’s not yet complete, but I make a point of carving out real time with each of them, not just a text when I’m in a bind.
“Evil can pretend to be good and kind, but good and kind cannot pretend to be evil. So when you see evil behaviour in someone, believe it. They are showing you who they really are.”
Building your boardroom isn’t only about who you let in. It’s also about being clear-minded about who needs to be shown the door. I’ve learned the hard way what it looks like when someone you’ve been vulnerable with uses that against you later, at the worst possible moment. You can’t blame a bad day or a difference of opinion, it’s a pattern, and once you’ve spotted it the smartest response isn’t to confront it. In my opinion, it’s distance. Stop handing them material. Stop helping them get a leg up. Your boardroom is for the people who’ve earned a seat.
Who’s in your boardroom right now?
Most business owners make big decisions one of two ways. Completely alone, wrestling it out in their own head at 11pm. Or by asking whoever happens to be around that week, whichever colleague, friend or Facebook group is closest to hand when the doubt kicks in.
Neither of those is a decision-making process. One is isolation dressed up as independence. The other is outsourcing your judgement to whoever’s loudest or nearest, regardless of whether they’re the right person to be weighing in.
A boardroom, whether it’s the internal one built from every version of you that’s learned something the hard way, or the external one made up of five people you’ve chosen on purpose, works because it’s deliberate. You’re not hoping the right perspective shows up. You’ve already put it in the room.
Who’s in your boardroom right now? Is it the loudest voice in your head, or the ones that have earned a seat? Is it whoever you happened to run into this week, or the five people you’d trust to tell you the truth and still be there tomorrow? You don’t need to trust your gut more. You need to know whose voices built it, and make sure the right ones still have a say.
If you’d like to be connected to the life coach I mentioned, please email me and I’ll introduce you.