5 Signs Your Side-Hustle Is About to Flop

Declan Wilson

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I had this idea.

It wasn’t just any idea. This idea was going to change things. This idea was THE idea.

I left the conference room in a hurry. The last 30 minutes of the meeting were a blur, something about production capacity or supply shortages. It didn’t matter. Eventually, when this idea took off, I’d no longer need a 9-to-5.

This idea was my escape…

Until it flopped. Miserably.

After leaving my 9-to-5 with high hopes, I ended up eating $26,000 of debt, struggling with anxiety, and wasting precious time and energy all because I should have seen the painfully obvious conclusion:

Not all ideas work out, most fail. The trick is to predict which ones will fail and walking away before they do more damage than good.

An exciting idea for a side-hustle feels like your own child. I should know. I have two kids and countless side-hustles. Sometimes it’s hard to tell them apart (that’s not true, my human children are easy to identify by their consistent nagging for more snacks).

Giving up on a side-hustle is like abandoning your own kin. It feels like a failure but in actuality, it’s a smart move. Having the self-awareness to know something is not working and the grit to give it up is not a skill that’s talked about.

The “American way” is to pull yourself up by the bootstraps and push forward no matter what. For some reason, we glorify struggle over smarts.

I’m sorry, but the “easy way out” is a viable option.

So, how do you know your idea is about to flop? As someone who’s experienced many flops, here are five common signs and what to do about them.

Sign #1 — It’s too original

Whether it’s art, service, or a physical product, the goal isn’t to be so original that your idea is unrecognizable.

The goal is to toy with people’s expectations while also creating something that feels familiar.

If your idea is too original and requires a lengthy explanation, then you don't have an idea, you have a problem.

Think of originality as oxygen.

The atmosphere has 21% oxygen and is perfectly safe to inhale. At 50% oxygen, our atmosphere would become too toxic to breathe.

Those seem like good arbitrary boundaries to keep in mind. Add in some originality, but not too much to make the idea toxic.

Sign #2 — It feels like something you *have* to do

You aren’t under any legal contractual obligation to work on your side-hustle. If it feels like something you have to do then something is not right.

You have to show up to your normal job to get paid (you don’t have to, technically, but just go with it). When your side hustle feels like drudgery, it’s time to re-think the situation.

A side-hustle should bring you joy. Not in every moment, of course, but overall the act of engaging your side-hustle should generate joy in and of itself.

And notice I didn’t say “profit” instead of “joy”. Your side-hustle can be as profitable as f**k but if it makes you miserable there will come a day when it will flop simply because it’s drained you of every desire to keep going.

Let’s set for ourselves a general rule of thumb: If your side hustle feels like a job, it’s going to end up like a job. Don’t waste your time.

Sign #3 — It’s too ambitious

Paul Jarvis wrote a book called Company of One and after reading it some year and a half ago, I’ve never looked at things the same.

“Economies of scale can sometimes be required for success in certain markets and for some products, but often they aren’t required and it is ego, not a strong business strategy, that is forcing growth where growth isn’t necessary.”
Paul Jarvis, Company of One

After I pre-maturely left my full-time job to “scale” my side-hustle, my main ambition to grow was fueled by ego. I wanted a big business and be the big CEO and have big new things.

Again, everything flopped because my attention was on the unattainable, overly ambitious what-ifs and not on the few clients I had.

Then along came Jarvis’s book, and not to brag, but I’m pretty sure he wrote it specifically for me. He talked about staying small and trying to be better instead of bigger.

That was my lightbulb moment. I let go of my business coach. I informed my “employees” (a handful of freelancers). I went line by line on my credit card statement and canceled any tool, service, or subscription that wasn’t critical to operation.

I stripped everything down to where I should have been all along.

If you have a good idea, focus on making it better, not bigger. Don’t feed your ego.

Sign #4 — It’s not profitable (or at the very least breaking even)

Think of your side-hustle as a little hole in a metaphorical boat. Your normal job acts as a siphon to remove any water that leaks into your boat so it doesn’t sink (I hope by now you realize the boat symbolizes your life).

Eventually, you’d like that hole to patch itself up. Even better, the boat grows a set of jet packs and wings and flies above the water rendering the siphon useless. (Okay, this metaphor isn’t adding up as I had anticipated).

What I’m trying to say is this: if your side-hustle is draining the bank, please have the courage to give up.

People tend to value sunk costs more than opportunity costs, which is absurd. The time, money, and effort you invested in a failing side-hustle are gone. You can gain any of those things back.

Instead, look at the opportunity cost of quitting. What if you shifted your time and attention towards a new side-hustle for the next 90 days? What could you gain?

Foresight is more important than hindsight in this situation. Quit while you’re behind.

Sign #5 — You know it’ll flop but you’re too afraid to quit

There’s a good chance that if you’ve read this far through the article you already have a gut feeling you’re afraid to acknowledge.

Your idea is going to flop.

First, let me reassure you. You aren’t dumb for believing in your idea. You aren’t a failure because it isn’t going to work out. You haven’t diminished in any way as a human.

Second, let me encourage you. If you’re afraid to quit because of what others will think about you, realize they probably don’t care as much as you think.

If you’re afraid of not knowing the next step, you’re smarter than you give yourself credit.

If you’re afraid of giving up too soon, then yes, there is a real possibility that I’m just some random dude on the internet who’s advice is not applicable. But I trust you know your situation better than I do.

Your idea isn’t going to work and that’s a good thing. It’s a good thing because it means you’ve grown as a person. It’s a good thing because you’ve let factual reasoning overcome emotional reasoning.

It’s time to let it go and move forward.

Starting over is the fun part

Fire up the creative engines. Dust off those old notebooks. Get to work on your next idea.

Take some time to mull things over. Learn as much as you can from your past ideas that didn’t work out and see what you can do differently this time around.

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Stay-at-home dad. 9-to-5 escapee. Aldi aficionado.

Baltimore, MD
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