The hard thing about hard decisions

I was recently faced with one of those big, brutal, high-stakes decisions. The kind that makes you rethink your entire trajectory—career, business, and even my identity a little.

These crossroads have appeared a few times in my 18-year run in business. Some turned out well. Others I look on with regret. Having gone through this a few times, I know how much weight these carry.

The act of deciding doesn't get much easier. But getting to other side is a huge relief. Now that I'm 2 weeks past making this decision, I'm feeling a huge sense of excitement and motivation about my future. But before I came to this decision, I was struggling.

It made me think about 3 key mindsets I try to use when working through big, high-stakes decisions. Here they are:

Undo-able Decisions

The first question I always ask: Is this decision permanent or undoable?

The truth is, most decisions aren’t permanent. You can quit. You can change direction. You can walk it back. So if the stakes feel high but the consequences are reversible, just make the call and move forward. The wrong move is often no move.

But every now and then, it really is a permanent choice. For example, the decisino to sell a business. Once you do it, it’s done. So these permanent decisions do deserve a bit more time and deliberation.

Be aware that some decisions masquerade as permanent decisions but really aren't. They just feel heavy in the moment. Many times, you're still able to course-correct.

Since most decisions are undo-able, you're better off making the decision one way or another, sooner rather than later. Waiting for information won't help you (it'll often lead to over-thinking).

How to Seek (and Use) Advice

Advice from trusted friends and mentors is helpful.

But there’s a wrong way to ask for advice: Asing, “What should I do?” isn't helpful.

No one can answer that for you. Even your smartest, most experienced friends can’t possibly know what’s right for you. Only you know that.

Still, outside perspectives can be helpful—if you know how to ask and how to use the feedback.

Rather than asking others to decide for me, I prefer to share where I'm leaning on this decision, then asking "How does that land with you?” I’m looking for reactions, blind spots, gut checks.

The best insights come from people who are closest to me and care about my happiness, not just my business strategy. I can think logically about my business strategy. But predicting my own happiness can be murky. My loved ones help me gain clarity here.

Struggle to Your Advantage

My most recent insight about decisions? Your best clue is your struggle itself.

If a decision feels especially hard, it might be because your gut is pulling you toward the less conventional path. That’s uncomfortable. Everyone around you might say, “Wow, this opportunity is incredible!” Logically, they might be right. But if something in you hesitates, you have to listen to that.

That’s exactly what happened to me recently. I was staring at what many would deem to be dream career opportunity. But it wasn’t clicking, for me. That internal tension revealed my true values. And once I accepted that, my decision became clear.

Struggle is often the breadcrumb trail to your gut instinct. Follow it. It’s usually right.

Owning your decisions is part of the deal when you’re building your own thing. I’ve made good calls and bad ones over the years, but every time, I’ve learned something important.

If you're in the middle of a tough call, I hope this helps you move forward with a little more clarity. Good luck and remember, you're this close to the other side!