Mistakes that Caused My First Side Hustle to Flop

I’ll be the first one to admit I failed at my first side hustle big time.

Thankfully I identified my errors before too much of my time was wasted.

Here’s some back story.

Dog walking was my first go around as a side hustling queen. Before this first side job my main source of income since 16 years old had been punching some sort of clock. I searched for a side hustle that was low pressure and didn’t involve tons of interaction with people, paid pretty decently, and allowed me to be outside during the summer.

I thought dog walking was the perfect gig.

However, my interaction with one specific client (let’s call him Tom) was a life-changing learning experience in self-employment, managing clients, and knowing when to throw in the towel on a failing gig.

Mistake #1. Being overly accommodating.

No one can run a successful business by being extra nice all the time. That’s a surefire way to get taken advantage of and thanks to Tom I’ll never forget how far people will push the limit if given a chance.

I should have known something was up when he refused to give me a key to his apartment.

Instead he asked me to use the call box when I arrived so he could buzz me into the building and requested I download an iPhone app to access his door so he could monitor my entry. I couldn’t download the app on my phone, so I had to switch phones with my husband each day.

Tom would get stuck in meetings and miss my call from the call box or answer his phone from home having forgotten to alert the walking agency that he didn’t need me – all trips I made that went unpaid.

The accommodating me continued to grin and bear the lackluster apologies, because they were honest mistakes. Right?

It gets worse.

Mistake #2: Not knowing my worth – every second.

Tom called me or texted me before or after walks to chat about how his dog was doing. Now I understand that dogs are pretty important parts of our families, but the time I spent in conversation about how much water I put in the dish after the walk was ultimately not worthy of my time.

Still I felt guilty not responding because I was indeed contracted to provide him a service. So until I found the guts to confront him and the agency I kept chugging along. But soon it felt as though I had morphed into Tom’s free dog walker and found that the seconds of my day were better suited elsewhere.

Mistake #3: Holding on to the bitter end.

Hind sight is 20/20 right?

I should have given up on Tom and walking for another hustle as soon as I realized its drawbacks. But there’s something in our psyche that tells us we should push through something for the good things that come through patience.

Not so with everything.

If you’re feeling like something isn’t working or it’s not worth your time don’t go along for the ride. You’ll miss more lucrative opportunities that could be more viable.

Looking back all the signs were pointing towards quitting, but the determined person in me felt like I couldn’t give up so easily. Although your situation may be less clear remember this – quitting isn’t failure.

Final thought – things go on without you.

After coming to terms that this hustle was a failure, I felt a little sad parting ways with his dog and figured he’d be hurt that I decided to cancel.

After all, we texted almost daily about his dog. I let the agency know I would no longer be available for that walk and I expected a message apologizing for the hoops I went through to accommodate him.

Nothing came.

If you quit a side hustle you may feel like you’ll leave someone hanging. Don’t. No matter how important your service is to someone, they can and will move on from you. Don’t let loyalty be the reason that you’re selling yourself short.

The one person you should be most loyal to is yourself!