They Can’t All Be Winners

When your side hustle needs to shift

Melissa Berdine
Jul 21, 2017 · 4 min read

Yesterday was one of those “pitfall” days every entrepreneur experiences. It seemed like everything that could overwhelm me did overwhelm me. The journey, where we are, finances, and above all, our side hustle: dog-sitting.

We currently have three guest dogs here, and there’s going to be a fourth today (though, one of the dogs here right now goes home today, so we’ll still be at a total of four dogs when we go to bed tonight, if you count Holly).

I first signed up for dog-sitting when I lived in NYC in 2015. I signed up honestly willing to do it for free, until I realized that the cheaper you set your prices, the more uncontrollable the dogs were that owners brought you. No matter, I raised my rates and got to get paid more and sit for better dogs. Awesome!

Since starting entrepreneurship, dog-sitting has become our main source of income. We do the meet-and-greets and hardly ever say no (unless the dog really is a nightmare, or we can tell Holly is terrified of one, which does happen on occasion). With it being our main source of income, it takes a lot of time away from us being able to actually focus on our businesses. When you’re essentially babysitting four to five pooches non-stop, making sure playing doesn’t escalate to fighting, making sure everyone is eating their food and only their food, perking up your ears to distinguish a playful grunt from a hostile growl. It’s a lot. It’s distracting. It’s time consuming.

I’ll be honest, I absolutely broke down in tears yesterday from all of it. It was Thursday, I had put in maybe 10 hours on our businesses this entire week, and that not only frustrated me, it downright pissed me off. I have no one to blame but myself. I signed up for entrepreneurship, I signed up for a stressful day-to-day, I signed up for all of this.

As stressful as yesterday was, it still beat a day in corporate America. Entrepreneurship is hard, but it’s still very much worth it to be able to see Steve during the day, build something great together, give Holly and guest dogs that would normally be home alone a little extra loving and playing.

With that, Steve and I do miss the days that we dog-sat purely for fun, when we could be selective, when it was just a little extra money for craft beer festivals and not money we needed for groceries. We want to go back to that, because when you have good, well-trained dogs that listen and that love Holly, Rover is so much fun (as I wrote this, Willy, a black lab, shredded Holly’s bed in the other room. Cool.)

Steve and I took the dogs on their walks last night and had a very productive brainstorm on alternative ways to make money that could very well pay us what Rover does (maybe more) with less of a lift, so that we can go back to enjoying Rover and putting in the hours that our businesses deserve and require. Today we’re earmarking 4 hours to go into Upwork.com and apply to freelance gigs, Steve is having talks with people to ghost write for occasionally, and I’m in communications with an agency to provide freelance work for them.

My mom always tells me “necessity is the mother of invention”. An invention isn’t quite what’s needed here, but it still translates. Steve and I are shifting our side hustle. Rover was working for a few months, but now it’s not anymore, and that’s ok. It’s not paying us what our time is worth, and it’s causing us additional stress that is exhausting both of us. Our side hustle should not be the thing that’s top of mind or our main source of stress. We’re absolutely relieved we communicated and checked in with one another and agreed that what was working once simply isn’t and we get to change it. Flexibility comes with the territory of being an entrepreneur, and even though we originally planned on going balls to the wall with Rover for at least six months, that’s just not sustainable or realistic for us, so we’re open to the fact that this is going to result in a shift in our plans. In fact, it’s going to work out even better than doing Rover for six months because we’re going to make it so.

Going through this is what’s going to make it all the more worth it later on. From this experience, we’ve learned to not cheat ourselves. To check in and make sure we are valuing our time for what it’s worth and trusting that our skills are enough to make a side hustle living on. To make sure that we are bringing in the most amount of money we can while providing the greatest amount of value to clients and ourselves.

Cheers to this week being over, a shift in side hustle, and enjoying the journey! Happy weekend, everyone! Go forth and chill as hard as this guy:

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

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Melissa Berdine

Written by

Denver by way of NYC by way of DC. Avid cook, lake bum, activist, cold weather enthusiast.

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

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