What Happens if You Start Over?

i've been thinking about this question for a while now.

not in a hypothetical way.. like actually sitting with it.

bc I've done it. more than once.

architecture school to design. design to development. development to systems building. each time feeling like I was torching years of progress to start from zero.

and each time.. the fear was almost entirely wrong about what would happen next.

🔬 the fresh start is a real thing

so here's something that made me feel less insane about all of this.

Katy Milkman at Wharton — she studies why people fail to follow through on their goals. and she found this thing called the Fresh Start Effect.

basically.. gym attendance spikes 33.4% at the beginning of each week. google searches for "diet" surge after new year's, birthdays, even mondays.

the psychology is kind of elegant. temporal landmarks create a mental boundary between your "old self" and your "new self." your past failures get filed away. you get a clean slate.

but here's the part that stings.

the effect fades.

monday motivation? gone by thursday.

new year's resolve? dead by february.

the fresh start isn't the hard part. staying started is.

which means.. you can't just rely on the feeling. you have to build something underneath it. the spark is free. the follow-through costs everything.

🌊 what actually happens when you blow it all up

idk if this is comforting or terrifying but..

Bruce Feiler spent years interviewing 225 Americans about their life transitions. and what he found basically demolished the myth of the linear life — one career, one path, one steady climb.

the reality:

five years. that's not a pivot. that's a marathon.

and he identified three phases every transition moves through:

I think about my own transitions through this lens now. the long goodbye from architecture wasn't a week.. it was months of knowing I was done before I could say it out loud. the leaving starts way before you leave.

🪞 the identity problem nobody talks about

this is the part that messed me up the most.

Herminia Ibarra spent years studying professionals in career transitions. and her conclusion upends everything the self-help industry tells you:

you don't think your way into a new identity. you act your way into one.

when you're in transition, you don't have one true self waiting to be discovered through journaling and personality tests. you have hundreds of possible selves. and the only way to know which one fits is to try them on.

I remember telling people I was "getting into web development" and feeling like a fraud. bc I still thought of myself as a designer. but Ibarra's research says that's exactly how it works — the identity catches up to the action, not the other way around.

you don't wait until you feel ready. you do the thing and let the feeling follow.

anyway..

💰 the sunk cost trap

here's the uncomfortable truth. most people don't start over too early.

they start over too late.

Annie Duke — former professional poker champion turned decision scientist — wrote an entire book on this. her thesis: we're systematically terrible at quitting because our brains are wired against it.

think about it. you've spent 8 years in a career. you've got the title, the network, the identity wrapped around it. walking away feels like you're throwing all of that in the trash.

but Duke's reframe is brutal and liberating:

waste isn't what you already spent. waste is what you continue to spend on a losing hand.

the sunk cost is gone. it's gone whether you stay or leave. the only question is what the next unit of your time is worth.

and when I left architecture.. the years I'd spent weren't wasted. the spatial thinking, the systems approach, the obsession with how things fit together — all of that came with me. you don't lose what you learned. you lose what you were pretending still worked.

🧭 the bezos question

in 1994, Jeff Bezos invented a framework to decide whether to quit his Wall Street job. he called it the Regret Minimization Framework.

project yourself forward to age 80.

look back at your life.

ask:

what will I regret more — failing, or never trying?

that's it. that's the whole framework.

and it works bc it cuts through all the noise — the spreadsheets, the pros and cons lists, the advice from people who've never made the leap themselves. it just asks the one question that actually matters.

🔄 what I've noticed about starting over

I'm not going to give you a numbered list of steps. bc that's not how it works and we both know it.

but here's what I've noticed from doing it multiple times..

the hardest part isn't the restart. it's the space between deciding and doing. that liminal zone where you've mentally left but haven't physically moved yet. Feiler calls it the messy middle. I call it the part where you question everything at 2am.

the people around you will be weird about it. some will think you're brave. some will think you're reckless. most will project their own fears onto your decision. their reaction tells you more about them than about your choice.

you don't need a perfect plan. Ibarra's research says the opposite — trying multiple possible selves through small experiments is more effective than sitting in a dark room trying to figure out your passion. start before you're ready. the clarity comes from movement, not meditation.

temporal landmarks actually help. Milkman's Fresh Start Effect isn't just academic trivia — use it. time your restart to a monday, a new month, a birthday. your brain is already primed to see it as a beginning. ride the wave instead of fighting the current.

the compound cost of staying is invisible. Duke's sunk cost work shows that we dramatically overvalue what we've invested and dramatically undervalue the opportunity cost of not moving. every month you spend in the wrong thing is a month you didn't spend in the right thing.

🚦 the real question

starting over is scary. obviously.

but so is the alternative.

staying in something you know isn't right and wondering, at 80, what would have happened if you'd been brave enough to find out.

I've started over enough times to know this:

the fear is always bigger than the thing. always.

the blank page isn't empty. it's open.

anyway.. the question isn't "what happens if you start over?"

the question is what happens if you don't.

-riley