Overachiever, You Might be an Entrepreneur

Experimental Side Hustles

I was an overachiever in corporate America. I wanted to crush every project, bring out-of-the-box ideas, and say yes to everything that came my way.

Why? Because I’m a do-whatever-it-takes kind of person.

But here’s the problem: Overachievers don’t always get rewarded in corporate jobs.

The Overachiever's Dilemma

There’s such a thing as being too valuable to promote. If you’re the one holding everything together, why would they move you? Promotions are about business needs, not just hard work.

And before you ask, I don’t believe working for yourself is the only way forward for overachievers. I’ll be posting another Substack soon on how to thrive in corporate if entrepreneurship isn’t your style.

But here’s my take: Overachievers need an outlet. We can’t just turn it off. And instead of cycling through the same disappointments at work or suppressing our ambition, I have a different solution:

Side hustles.

Why Side Hustles Work for Overachievers

A side hustle is your world. You’re the boss, the visionary, the engine, and the decision-maker. No pointless one-on-ones with your boss disrupting your flow. No bureaucratic red tape killing your ideas. No performative deadlines. You control the pace.

Side hustles gave me relief from the box I was trapped in at work. I could learn new skills without waiting for permission. In corporate, promotions and job changes take months, sometimes years. But when you’re building something on your own? You control the speed, the scope, and the goal.

It’s upskilling at the highest level. And yes, side hustles got me jobs. That’s how I landed my lazy girl job at Wix. I literally had the recruiter pull up my old Wix account where I made websites for family friends in college during our interview.

The “Experimental Side Hustle” Mindset

Stop overcomplicating it.

You don’t need a business plan.
You don’t need an LLC. (It takes two seconds to set up later. Worry about that when you need to.)
You don’t need the perfect name.

All you need is a mindset shift: Treat your side hustle like an experiment.

This isn’t an urgent work report.
This isn’t a performance review.
This isn’t a corporate project bound by rigid KPIs.

It’s your playground.

So next time you feel that itch to overachieve at work (I see you volunteering to take notes in the meeting - knock it off, AI can do that), redirect that energy. Hold onto it for those two cozy hours you’ve set aside at the end of the week to work on your own thing.

No Expectations, Just Learning

Side hustling isn’t about immediate success. It’s about learning, which leads to more power and autonomy later.

And that’s exactly how I became the Anti Work Girlboss.

This all started as a creative outlet. In 2021, I was just posting TikToks about breaking into tech for non-technical people. I didn’t even come up with “Anti Work Girlboss” until over a year later.

I started by learning how to brainstorm, film, and post a video once a day.
Then I discovered Linktree and figured out what links I could embed to sell or teach my audience something.
Then I learned how to read analytics.
A link view vs. a click? Okay.
What percentage of people actually clicked? Cool.
Is that number good?

I just nerded out slowly over time.

So if you’re thinking, Well, that’s easy for you to say, you already have followers!—Girl, I started at zero too.

Here’s a photo of my account in 2021 for proof:

First rule of entrepreneurship: Never judge your Day 1 against someone else’s Day 1,000.

In corporate America, they pit people against each other for promotions. Entrepreneurship doesn’t play by those rules. If you constantly compare yourself, you’ll burn out fast.

Let’s Make Your Day 1 Easier

Don’t know what niche to pick?

Day 18 of the Lazy Girl Job Challenge has ideas for you ⬇️

Have an idea but don’t know how to turn it into something sellable?

The Lazy Girl Side Hustle Guide takes you from idea to product in 7 days. One small, non-overwhelming task at a time.

You don’t have a product to launch?

Cool, start consulting first. ⬇️

I bet after you talk to 10 clients, you’ll get a better idea of common problems you can solve for at scale.

Already have a product to launch?

Get a done-for-you link in bio website with Planoly. Be sure to use my code ANTIWORK for 30% off all plans!

I made a store front with them in 5 mins. You can learn more about Planoly below ⬇️

antiworkgirlboss

A post shared by @antiworkgirlboss

My Final Words

Absolutely no one is going to tell you to start an experimental side hustle.

I waited an embarrassingly long time to take mine full time for one reason. I was waiting for permission.

In corporate, we’re trained to seek approval before taking on anything new. That conditioning bled into the rest of my life.

I caught myself waiting for my boss, my boyfriend, my therapist (not even kidding), and anyone else who would listen to my job complaints to anoint my side hustle as worthy.

But here’s the truth: No one is coming to give you the green light.

At first, that realization feels terrifying. But over time? It starts to feel limitless and even empowering.

So if this post gave you any sense of relief or inspiration, consider this your sign. Congrats, you’re officially the chosen one.

Go start. I’m always here if you need help!