I Went Back to Meet 2015 Me
I'm sitting on a flight to NYC right now. You don't appreciate the luxury of flying solo until after you have kids. Being able to put on headphones, ignore the world, and lock in for a few hours is genuinely a treat.
But somewhere over the midwest, I stopped working and started thinking. Because NYC is where it started. Tiny apartment, 2015. And BestSelf just turned ten.
The Time Travel Day
I came across a concept recently called a Time Travel Day.
The idea: pick a past version of yourself and invite him/her into your current life for a day. You narrate it to them. Drive around and explain why you live where you live. Who's in your life now. You listen to their music and just revisit your past self for a bit.
If you're reading this, you're likely ambitious and always striving to move forward. The goal posts keep moving because that's what we do. But it's only when you turn around and look back down the mountain that you see how far you've come.
Flying to the city where it all started felt close enough.
How It Started
Tiny New York apartment. 29 years old. Freshly wrapped Kickstarter, $322,996 raised (way more than I expected, honestly terrifying), convinced the whole time it wasn't going to work.
That version of me didn't think she was starting a company. She just wanted a product to exist. She'd been jamming her own planning structure into a plain Moleskine because nothing else fit how her brain worked, and she thought: what if I designed this properly?
So she did. And then 10,000 people said they wanted one. That's when she thought: maybe this is something?
If I had to pick one thing to tell her, it's this: the years that look like winning are going to feel like drowning too. You don't have to choose one, and there are levels to it all.
She'd win the Shopify Build a Business competition in the first year. Play Monopoly with Daymond John. Ring the NYSE bell. Her parents, who watched her leave Ireland alone, quit architecture, and bet on herself in a new country, they'd stop worrying… but probably not.
And in those same years: a business partner who mentally checked out but kept 50% for three more years. A divorce in 2017, the same year BestSelf looked from the outside like it was thriving. In 2020–2021 a team member later convicted of embezzlement. Container costs going from $4,000 to $24,000 overnight. Selling to private equity in 2022. Then buying it back when they nearly ran it into the ground in 2024.
Both of those things were true at the same time. I wanted to say that plainly.
2015 Cathryn thinks success means everything is working. She's going to learn that's not how it goes, but also you level up and learn how to better deal with bigger problems.
Here's what surprised me about the Time Travel Day. It wasn't the advice I'd give her. It was realizing what she already knew that I'd stopped trusting.
She was building because she wanted the thing to exist. Not for the revenue. Not for the exit. Because she couldn't find it anywhere else and she thought other people might need it too.
Somewhere along the way I drifted from that. Chasing revenue meant more products. More products meant faster timelines. Faster timelines meant showing updates in five days instead of solving problems that actually took years.
She knew the thing I keep forgetting: the best things we've built came from following problems, not filling product slots.
The Self Journal because I couldn't make my own days feel coherent. (I got an ADHD diagnosis in 2018. It explained a lot about why I'd spent years building structure tools just to function.) Helm because customers kept telling us they knew exactly what they wanted and still couldn't focus long enough to get there. The Self-Discovery Deck because people stopped knowing what they wanted at all.
Three things: know yourself, plan yourself, protect your focus. We built all three by refusing to stop asking what was actually getting in the way.
2015 Cathryn is doing exactly that. She just doesn't know yet where it leads.
There's one more thing I'd tell her: get the ADHD diagnosis sooner. She's going to spend years building systems for her brain before she understands why she needs them so badly. She's going to feel like she's cheating the whole time, like she's the only one who needs this much scaffolding to get through a day.
She's not. The scaffolding was the point all along.
Pick an age. Not the safe one. Not the confident, put-together version. The one who was uncertain and full of questions you've since pushed aside.
Spend 30 minutes narrating your current life to that person. Tell them why you live where you live. Tell them who's in your life now. Tell them what took longer than expected, what surprised you, and what they'd be proud of.
You don't need the answers. Just notice what they'd want to ask you.
What would your 10-years-ago self be most proud of about where you are now? And what are you not giving yourself credit for?
