The New Year's survival guide for creative overthinkers
How I finally started the project I'd been putting off for years
In September 2023, over drinks with Philip Allen Bennett, I told him about my dream of starting a podcast. I’d been thinking about it for literally years. A few days later I text him, absolutely spiralling about how to make it work (I’m cringing even reading this again, but I hope that’s a sign of growth). His response was amazing:
He wasn’t being mean. His baby was due! But it worked.
I didn’t have a plan or know anything about making a podcast, but Phil knew a studio we could rent and was willing to give his time and energy to show me the ropes and record an episode in the process. And the deadline was absolutely not negotiable. So we did it!
I try to think of this whenever I’m overthinking something. The best way forward is almost always to tell myself “you have two weeks”.
Three escape routes from overthinking
New Year’s carries a weird energy. It’s the weight of possibility. I both love and hate it. The good news is that if you’re feeling a pull to “finally do something”, you’re already halfway there.
I’m currently in Potsdam, Germany. My girlfriend and I come here every New Year to hike, journal, and think without Berlin’s chaos. And every January 5th, the imperfect.club domain renews (it took me 3 months from recording that episode to picking a name - yes, I was overthinking it again).
The name, and the renewal, is a permanent reminder that nothing I do has to be perfect, including the names I give things. I just have to start.
Looking at my journals from previous trips to Potsdam, I noticed a few prompts that help me go from “thinking about it way too much” to “actually doing it”:
1. What could go right?
Most of my overthinking is just fear. Fear of failing, of looking stupid, of wasting time. Buried under that fear is genuine excitement about what could happen. What I did right before buying the domain and publishing that first episode was to grab a piece of paper, write “what could go right?” at the top, and then write a long list of things I was excited about that could only happen if I started.
Fear and excitement tend to show up together when there’s potential for growth. I’ve learnt that starting is easiest when you tilt the scales in favour of the excitement.
2. What makes this time different?
If you keep setting the same goal year after year, something’s in the way.
I’ve said I want to “get fitter” for the last five years. I’d been “thinking about starting a podcast” for even longer. It’s easy to blame discipline or motivation. In reality I hadn’t figured out what was actually stopping me or what I really wanted.
With fitness, vagueness has been the problem all along. I can’t tell if I’m making progress because I’ve never defined what “fit” means. Squat my body weight? Run 5k? Without that clarity, even real progress has felt like failure.
With the podcast, I didn’t know how to start, and I was scared. So I just kept thinking about it. Phil removed both barriers by showing me how it worked and giving me a deadline.
One technique I’ve found useful is the “future-retro.” Pretend it’s six months from now. You didn’t do the thing. Why? Write it down, address it now, and then start.
If the answer is “because I don’t actually want to prioritise this,” then great, don’t do it. Remove it from your list and stop feeling guilty.
3. Can you start it today?
There’s a few things I’ve done within hours of returning from Potsdam. One was buying the domain. Another was setting up an ETF savings plan I’d been “meaning to look into” for months.
I gave myself one hour and it took twenty minutes. Most things you’re overthinking can be started literally today. Even if starting means the smallest possible step.
Let the excitement get you started. Don’t worry yet about whether this will work long-term or what systems you’ll need.
The summary of all of this is if you’re feeling that New Year’s motivation to change or start something, do that thing right now as imperfectly as you can.
When you start doing the stuff you’ve always wanted to do, you realise there’s no secret. You just have to do it and see what happens.
Overthinking is the enemy of good work actually getting done.
Pretend you just got Phil’s message: You’ve got two weeks.
On the podcast
Season Two of the Imperfect Creatives podcast kicks off on January 7th! The first episode is with the wonderful Rick Foerster and I am sooo excited to share it. Being able to chat with people like Rick was absolutely on my “what could go right” list.
We talk about Rick's journey from working at startups and being a high-level executive to quitting and writing a post-apocalyptic fiction novel, his fantastic writing here on Substack, finding meaning in our work, and more.
If you don’t want to miss it, you can subscribe on Spotify, Apple, YouTube (this will be the first video episode!) or wherever you get your podcasts.
Good stuff this week
A huge shout out to Philip Allen Bennett for being a great friend and mentor over the years and giving me more than the odd push or two when needed. Go hire him for his leadership skills here and read his genuinely fantastic book “Punk Leadership” here.
The roads not taken - Becky Isjwara on leaving her investment banking job to work for a YouTuber, and taking hard lefts when something pulls at you, “illogical” or not. I look forward to Becky’s newsletter every week, and this one feels particularly relevant this week concerning the topic of finally doing things (fun fact: this newsletter used to be called “Roads Untaken” for similar reasons).
For Christmas I got Art Work: On the Creative Life by Sally Mann. I’m a third of the way in and loving it. She makes the case that writing is essential for thinking, unblocking, and recording your life, regardless of your creative medium. Since starting to write every week for the past year, I’ve realised how true this is. It’s a weekly practice that helps me find clarity, and having something to look back at shows me how my thinking has changed over time.
How My Career Break Failed & Why That Failure IS the Point - another great post by Sinem In Flux about what career breaks are actually like and what they really give you.
life is a crying baby. A container for ideas created during a specific time, sent to you as they were thought up. I love this project by Alex Dobrenko`. Creative, fun, and different. Feels like a great example of “just go do the thing and put it out into the world without overthinking it to death”.
Unrelated to everything else here, Four Tet does a set for TheLotRadio every year in December and I always look forward to it. This year’s is amazing as always.
And finally, a good note: