The Dark Side of Building a Side Hustle
Confronting identity, fear, and guilt
No one told me that building a side hustle feels like sneaking out of class. My heart’s racing, I’m terrified of getting caught, and I can’t shake the guilt that I’m missing the education my parents sacrificed so much for.
The Identity Crisis
I remember the look my banking colleagues gave me when they learned I was writing a book on the weekends. They gave me a “huh…” expression. I felt like I was exposed as a double agent: too ‘creative’ for a bank but also too ‘white-collar’ to be a best-selling author.
Building something on my own is going down an unpaved path. A pathless path, if you will. There are many directions I can take, none of them “conventionally” correct. It requires me to confront what I truly want, even if it means going against what others believe is “good” for me.
And in the heart of all of that lies the big question, the three words that kicked off the Severance series:
Who are you?
When I clocked out from my buttoned-up corporate persona and slipped into my energetic, on-camera personality, I sometimes wonder - which one of these am I?
I am both but I am also neither, because I oscillate between my innie and outie depending on what time of the day it is.
Some people take the cold plunge and quit their corporate jobs to start their own thing. I’m a bit more risk-averse than that, so I was two-timing.
I thought my creative self was a hobby the same way that people make foodie Instagram accounts or play football on the weekends.
But I knew I was building a raft I would eventually want to hop onto to sail to where the sky meets the sea because it calls me.
But of course, the thought of secretly building a raft is scary af.
The Fears
The first fear is judgement.
What will my colleagues think of me? Will they scoff at my “hobbies” and chalk it up to naiveté because I’m young and haven’t experienced enough of the corporate world? Will they think I’m wasting my time?
The second fear is that of wasted effort.
Who am I to be an author, an entrepreneur? To build something that will not sink? To be able to learn what pieces of wood go together so well that no water seeps through? But worse, what if my raft actually floats?
The third fear is that I succeed.
Because what will it demand of me then? Does that mean I have to keep steering my own ship? Am I even good enough to be responsible for myself, and potentially other people that will join in my crew?
The Guilt
I would carry those fears, all while continuing to belief that this raft will turn out to be something. But every pursuit means giving up a pursuit of something else.
Like drinks with friends. Weekend trips. Not working overtime on that seemingly-urgent-but-not-important work project.
I’ve been saying “cheat on your job” very cheekily but it really does feel like that. Just like how I feel two-timing a gym instructor, it does not settle well within me that I’m splitting my energy between my day job - one that I signed a contract for - and myself.
Outside the zone of comfort is discomfort
Doing new stuff is scary, because the range of outcomes is just so unknown.
I could write an article about a bank’s quarterly earnings, for example, and I know it would hit the mark. It’s because I did it for seven years. I know to look for fee income, loan margins, and assets under management. I just know it well.
But here on Substack, I don’t know what essay would hit the mark. And stepping out of an area I’m familiar with brings all sorts of discomfort.
But these feelings that are a bit hard to sit with are signs of expansion, not evidence that I’m doing something wrong.
As hustle bros would say, discomfort is the entry fee for growth.
Moving through the feels
There are some ways that have helped me navigate the lesser-known, darker sides of building a side hustle.
Journaling: Writing down the feelings is to acknowledge that these feelings exist, which is the first step to actually sitting with them and figuring out why exactly they are uncomfortable.
Building my tribe: I don’t know a lot of people IRL who are building side hustles, but I know a few online. I talk to them often. We share stories. The journey feels less lonely with comrades.
Finding mentors: Reaching out to people who are several steps ahead of me really gives me comfort. They’ve navigated this before and know how it feels. They can also give feedback on what I’m building.
Here comes the sun, doo doo doo doo
The great thing about the sun is that it shows up each and every day, and after the darker moments of building a side hustle, some brightness will come.
Sounds cheesy as heck, but playing the long game, aka outlasting a lot of people who try something and drop it, is a viable strategy.
So in case you’re still fumbling over your raft, keep at it.
Once you jump on it, you might just spot some other rafts sailing alongside you.
This is part of an essay series called Cheat on Your Job. If you’re up for it, what are some feels that pop up in your side hustle journey? Share them in the comments, or lemme know what you’d like to read next!
Update log:
🌎 On the
pod: Should you be consistent, or should you prioritise quality? and I get kinda nitty gritty with the details of our (abandoned) projects.📘 Finished reading $100M Offers by Alex Hormozi. What a gold mine. I’m now going through both the book again and his online course to absorb more of the material.
😮💨 Felt really down about my Hyrox performance but I’m picking myself back up by going back to the gym… slowly…
🎞️ Got my scans from the Ektachrome 100D film back. The colours are gorgeous
🗺️ Met
for the first time last week! We had been working together (and texting each other daily) for more than a month now. So surreal to see folks jump out of the Zoom screen.🎉 We hit 500 subscribers on Substack! This is so wild!! Thanks for sticking around for the journey 🥹
Book a call: Have a bite-sized creative project? Let’s give you a starting line boost a la Mario Kart - https://www.beckyisj.com/consulting
Some links are affiliate links, meaning that I may receive a commission if you make a purchase through the links at no cost to you.
This captures the weird mix of feelings of doing your own work on your own terms and at least for me it never quite feels normal. I’ve just eventually learned to embrace the full range of feels
As someone currently at the end of the journey you’re on, sort of, who is transitioning roles from one thing to another, I can really relate to what you’re saying. The only thing that I can say is that, the only thing I regret is places I didn’t show up or commit in my “job” because I was always scanning the horizon, planning an escape. I did all my duties—excelled at that, but personally I knew there were things I left on the table and that dogs at me, and the skills/relationships I could’ve built but didn’t bothers me. It was only corrosive to me in the end. It doesn’t sound like that’s in play here but just wanted to offer my $0.02.