Most of the founders I work with are not stuck because they lack ability. They are stuck because they are asking the wrong questions.
Over twenty years of building businesses and sitting across the table from people wrestling with hard calls, I have seen the same two states again and again. One founder is paralysed by a decision they cannot seem to make. Another is drowning in stress over something that is eating them alive.
Different problems on the surface. The same root underneath.
Neither of them is weak. Neither is short on capability. They have simply framed the problem in a way that makes it unsolvable. And the fix, in both cases, is not more information or more courage. It is a better question.
Here are the two I come back to, over and over, with founders, with friends, with anyone who will listen.
The First Trap: “Will I Regret This?”
Watch a founder circle a big decision and you will almost always hear the same question surface. Should I make the hire? Should I raise the price? Should I let go of the client that is draining the team? Should I put up with poor performance? Should I step out of delivery and trust someone else to run it?
The instinct, the responsible-sounding instinct, is to ask: “Will I regret this?”
It feels like the mature question. The considered one. The one a sensible person asks before they leap.
It is a trap.
That question pulls you backward. It asks you to picture a future version of yourself looking back with disappointment, and then decide based on a feeling you cannot possibly know yet. It is heavy. It is paralysing. And because you can never actually answer it, you never move. You just keep circling.
I have watched founders lose years to that question. Not because the decision was wrong, but because the framing made it impossible to make at all.
The reframe is almost embarrassingly simple. Instead of “Will I regret this?”, ask:
“What if I do not do it?”
Same decision. Completely different energy.
You are no longer imagining a hypothetical future regret. You are looking squarely at the alternative. What does it actually cost to stay exactly where you are? What do you miss? What stays broken? What still does not get built?
And here is the thing I have found almost every single time. The answer to “what if I do not?” feels worse than any risk involved in doing it.
The hire you keep delaying. What if you do not make it? Another year of being the bottleneck.
The price you know is too low. What if you do not raise it? Another year of undercharging for work you are proud of.
The client draining your best people. What if you do not have the conversation? Another year of your team quietly burning out.
Suddenly the decision is not so hard.
When I left my last role with nothing lined up and started Addoli, I spent longer than I would like to admit circling the decision. Was it the right time? Was I mad to turn down the offers of employment? All the usual questions, and underneath every one of them, the same quiet one: will I regret this?
I announced it on LinkedIn, which felt like stepping off a kerb without looking.
Within the hour a message came in from someone I had not spoken to in six years. She used to work for me. Just seven words:
“Well about bloody time!! This is exciting!!”
I had been asking “will I regret this” for weeks. What if it did not work out? She had answered a different question entirely, one I had not had the nerve to ask myself. What if you do not do it? What was I actually protecting by taking the safer option? She could see it in seven words from six years away. It took me far too long to see it from the inside.
This is not about being reckless. It is not a licence to leap at everything. It is about refusing to let the weight of imagined future regret hold you in place. You give yourself permission to act, because you have finally looked at the real cost of standing still.
Regret lives in the past, and you cannot go back there. Leave it behind you and learn from it. So stop asking a backward-looking question. Turn it into a forward-looking one that actually helps you decide what to do now.
The Second Trap: Spinning on What You Cannot Control
The first reframe is for the founder who cannot decide. The second is for the founder who cannot switch off.
A lot of my work, and if I am honest a fair bit of my life, is people bringing me exactly this. Not a strategy question. A knot. Something eating at them that they cannot put down, and they want someone to think about it calmly with them. Over the years I have noticed I end up saying the same thing almost every time.
In life, there are things you can control and things you cannot. Focus on the things you can control, because that is where you can actually make a positive change.
It sounds almost too simple to be worth saying out loud. But watch what it does to someone carrying the wrong load.
You know the state. Something is gnawing at you. You are lying awake with it, turning it over in the shower, carrying it into every meeting. And it is not making anything better. It is just draining you.
When someone brings me that kind of stress, the first thing I usually ask is one question:
“Can you control it?”
If the answer is yes, then good. That is exactly where your energy belongs. Plan. Act. Make it better. Stress that points at something you can change is just unspent action. Go and spend it.
If the answer is no, then you have to do the harder thing. Accept it, and let it go. Strength is not lifting everything. It is knowing what to put down. Not because it does not matter. Because spinning on something you cannot change does not fix it. It just quietly empties your tank.
Almost everything that lands on a founder’s desk falls into one of two categories. Things you can control, and things you cannot. A difficult client who will not be influenced. A market shift you did not cause. A regulatory change nobody asked for. A competitor doing something you cannot match.
You still have to deal with all of it. But pushing harder at the part you cannot move is just hitting your head against the wall. It exhausts you when the wall will not budge. Change what you can control instead, and the way around it usually appears.
The moment you can see clearly which category something belongs in, the stress starts to ease, because you stop wasting energy fighting something that was always beyond your reach. You take everything that was uncontrollable, you set it down, and you pour what is left into the things you can change.
Most founders I meet are carrying a rucksack full of things they were never going to be able to lift. The relief is not in lifting them. It is in realising you are allowed to put them down.
Why These Two Belong Together
On the surface they solve different problems. One is for indecision. One is for stress.
Underneath, they are doing exactly the same job. Both stop you spinning on things you cannot change, and redirect your energy toward the things you can.
Regret spins you on the past, so you reframe it into a question about the future you actually control. Stress spins you on the uncontrollable, so you separate what is yours to fix from what is not and pour yourself into the former. Same move. Different direction.
And here is why this matters more for founders than for almost anyone else.
In a founder-led business, you are the person the hard calls funnel to. The big decisions, the ones nobody else can make, land on you. The stress that comes with owning the whole thing lands on you too. You do not get to delegate the deciding. You are the bottleneck by design.
Which means these two traps hit you harder than they hit anyone on your team. The founder frozen by “will I regret this?” is the reason a good business sits on a plateau for another eighteen months. The founder drowning in what they cannot control is the reason the business cannot get the best of the one person it depends on most.
Getting unstuck personally and getting the business unstuck are, more often than not, the same task.
These are not grand philosophical ideas. They are two practical questions I use most weeks, on myself as much as anyone. They will not solve every problem you have got. But they will stop you being paralysed by the ones you cannot, and free you up to move on the ones you can.
Next time you are circling a decision, do not ask whether you will regret it. Ask what it costs you not to.
FAQs
How do I stop overthinking a big business decision?
Stop asking whether you will regret it, which is a backward-looking question you can never answer. Ask what it costs you not to act. Looking squarely at the price of staying still usually makes the decision obvious.
How do founders deal with stress they cannot control?
Ask one question of whatever is gnawing at you: can you control it? If yes, that is where your energy belongs, so plan and act. If no, accept it and put it down. Spinning on something you cannot change does not fix it, it just empties your tank.
