You’ve been here before.
You started the business, again. Rewrote the resume, again. Committed to the habit, the diet, the boundary, again. And then, right as things started to move, something happened. You ended up back at the beginning.
You probably call it bad luck. Or bad timing. Or bad discipline.
It’s none of those things. It’s self-sabotage. And it’s more logical than you want it to be.
Square One Is a Sanctuary
Here’s what nobody tells you about starting over: it feels safe.
Square One has low expectations. Nobody’s watching yet. The pressure hasn’t built. You know this terrain; you’ve mapped it a hundred times. You know exactly how hard to grind to survive here, and that grind feels righteous. Productive. Forward moving.
Except it isn’t moving forward. It’s moving in circles.
And here’s the part that stings: you don’t retreat to Square One because you failed. You retreat because reaching the next level felt unsafe. The grind doesn’t scare you, growth does.
The Research Trap
Pay attention to what you do right before you sabotage yourself.
You probably call it “getting ready.” You take a course, read the book, watch the tutorials, map out the strategy one more time. You tell yourself you’re preparing. But look a little closer, what you’re actually doing is controlling, and tiring. You’re constructing a fortress of information so that if things go wrong, you can say you did everything right.
Research mode is where capable people go to hide.
It looks like diligence. It feels like diligence. But it’s a way to stay in motion without taking the risk that growth actually requires. You can spend months, even years, in research mode and never feel like you’ve wasted a day. That’s what makes it so effective as a hiding place.
The next time you catch yourself saying I just need a little more time to prepare, ask yourself honestly: is this preparation, or is this protection?
Someone Handed You That Bill
Now we get to the part that matters most.
You’re not retreating to Square One because you’re lazy or weak or broken. You’re retreating because some part of you believes you should stay there. That you haven’t earned the next level. That if things actually worked out, something bad would eventually happen to balance it.
That belief didn’t come from nowhere.
At some point in your life, someone handed you a story. About who you are. What you’re capable of. What kind of person gets to succeed. You didn’t write that story. You were handed it, by a system, a relationship, a moment that landed harder than anyone intended. But you accepted it, and then you started paying it forward.
Every time you get close to something real and then pull back, that’s the payment. Every time you find the evidence confirming the worst things you’ve told yourself, that’s the payment. You are funding a debt that was never yours to carry, heck when it was given to you, you weren’t even old enough to apply for credit.
And here’s the hardest part: the guilt and shame embedded in that story don’t feel like a debt. They feel like truth. They feel like self-awareness. Like realism. Like the responsible, humble version of yourself keeping you in check.
They aren’t. They’re a tax you’ve been paying on someone else’s accounting error.
This Is the Direct Part
You are not being asked to perform self-confidence. You are not being asked to pretend the hard things didn’t happen.
You are being asked to stop being mean to yourself on someone else’s behalf.
You are being asked to notice that the voice telling you this won’t work, you’re not ready, who do you think you are, that voice is not your voice. It was set on your shoulders and you borrowed it so long it feels like yours. It isn’t.
Resilience isn’t about grinding harder. It’s about asking yourself: where am I denying myself forgiveness? Because the grind you’ve built at Square One, the research, the preparation, the “just a little more time,” it’s all armor. And armor is heavy.
The path forward isn’t more effort. It’s clarity. And clarity requires you to be willing to be wrong about the worst things you believe about yourself.
That is uncomfortable. It is also the only way through.
Start Here
You don’t have to throw out the armor today. Start smaller.
Write down three things you’ve said to yourself recently. The ones you wouldn’t say out loud with others around; especially those most special to you.
Now ask: are these actually true?
Not “do they feel true.” Not “are there moments that seem to prove them.” Are they actually, verifiably true?
If not, and most of the time they won’t be, write down three pieces of evidence for the opposite. Not affirmations. Not wishful thinking. Real evidence that already exists in your life that contradicts the mean story.
You’re not trying to convince yourself of something false. You’re just asking whether the accounting is accurate.
Most of the time, it isn’t.
Square One is comfortable because you know how to survive there. But you were built for more than survival.
You already know that. Some part of you has always known that.
That’s why you keep starting over.
LaSchwann Killens is an ICF-trained life and executive coach and the founder of VALADD Coaching. He works with people who are ready to stop waiting for permission and start making decisions that are actually theirs.