Side-Hustling For The Tired, Old, and Annoyed

I deeply admire those who have a good side hustle going for them. I know several people who are living the side hustle life and are very good at balancing their daytime work with their nighttime hustle.

I struggle with it. It’s such a delicate balancing act.

I once was told by a seer that one of my spirit animals is an elk — I go hard for days, and then fizzle out. I need to retreat into a dark cave to recover before I can go back out again.

There isn’t much nuanced side hustle how-tos for us elks — those of us who are too tired or bogged down with responsibilities and don’t wanna work into the wee hours after already working a long day.

As I’m coming more at peace with the fact that I don’t have the energy of a 20-year old anymore, I’m having to create my own playbook on how to sustainably side hustle. Here are some things I’ve been learning —

Side Hustles Don’t Have To Cannibalize Your Free Time

Defaulting to work-whenever-I-have-time hasn’t been working for me. I don’t work in a style that allows me to do a little every day.

I’ve looked at when I’ve been most productive, and it always seems to be the times when I’m working remotely out-of-town, get up before 7, or when there’s a long holiday weekend. It’s the times when there aren’t errands, social events, and house chores to take care of — it’s when my mind is cleared enough to focus in without FOMO.

There’s a preconception that in order for side-hustles to work, you have to be able to do a little every week. This isn’t true. A side-hustle routine can work around you rather than some made up notion that the hustle has to tag on after your day job.

If you’re drained after a long day of work, don’t create a soul-crushing grind by adding on more work. Get creative with your planning — measure your success by what you accomplish at the end of 365 days. Don’t measure it by how your efforts look on a day-to-day.

If You’re Not Excited, Pivot

Life is too short to spend your free time on something that doesn’t excite you.

If your side-hustle doesn’t incite pride or thrill, here’s what’ll end up happening — you’ll work on it for a short while, and then it’ll start to feel like a drag. You’ll lose momentum and eventually stop working on it.

No one ever produces their best work when creating from an already-tapped tank. In order to rise above that, the work has to align with your passion and fuel you with otherworldly purpose.

Pivot as much as you need until you find that. Pivot until it sparks your joy.

Avoid Burnout

It’s important for elks to have that assurance that the sprint will end soon and that there will be a rest stop. That’s how I try to contextualize my side hustles — I try to define them into project milestones rather than a dreadful neverending jaunt.

When mapping out quarterly goals, I also map out quarterly breaks.

Even if it’s just a few days, intentionally bake in definitive ends (so that you can celebrate them) and a breather to give yourself mental relief from needing to constantly work on your hustle.

It’ll help you meaningfully manage your energy for the long-term and keep you in the clear of experiencing the dreaded B-word — burnout.

For more wisdom that turns your startup chase into a victory lap, get my Friday emails, (lovingly called The Crux) in your inbox.

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