How I Left My Retail Job & Started to Work For Myself

I try not to mention that I work for myself very often because people get the idea that I make a ton of money, which isn’t true. I’m not doing terribly, but I’m still at a pretty early stage of figuring this whole thing out.

I still work 3 hours a day on weekdays as a nanny, but I make a decent amount of money between that and my freelance projects for the amount of time that I work each week. For me, the freedom I have to do what I need to do every day, like finally finishing my degree and working on my own creative projects and supporting my husband at his insane job (which we’re working towards getting rid of, too), is far more valuable to me than having an impressive salary. Because — spoiler alert — I really don’t give two shits who I impress anymore.

I worked in retail for twelve years. TWELVE. There were a few other jobs sprinkled in there, like some admin work and social media management, but for the most part it was retail. I used to think I wanted to manage my own store, but when I actually got into management, I realized that there’s almost no amount of money that would make me happy in that role. I loved being a manager but I just don’t have a connection with retail.

The last year I spent at my job was the hardest. I knew I wanted out but I had no idea what else I could do because I hadn’t finished my degree (and still haven’t — I only recently went back to finish it up and I’ll have it this December). I’ve always wanted to be my own boss, but I didn’t know where to start and I didn’t have the time or mental space to do it while I was still working at my last job.

The Question That Led Me to More Freedom

The question that led me to my eventual freedom came to me when I was spending another $8 on lunch one day when I was at work. It hit me that I spent $5–10 almost every day at lunch time, $2–5 on coffee and snacks, and another $30–35 on takeout most nights because my husband and I were too tired from work to cook, let alone muster up the energy to go on full blown grocery shopping trips. When what you’re bringing home after taxes and healthcare every day is in the $120–130 range, spending up to $30–50 a day on just making life feel normal is way too fucking much.

On top of that, I would buy shoes and bags and makeup to feel better about having to work. Not incredibly expensive stuff, but just enough to leave me with almost nothing left over, because what was the point of spending most of my day getting yelled at by customers and not seeing my family and friends if I didn’t have anything to show for it other than paying bills and rent?

Because my spending at work and because of work (and because I was so unhappy) was putting me in a situation where I was living paycheck to paycheck, I was convincing myself that I needed to make more somewhere else if I were to leave because I wasn’t paying attention to why I was living paycheck to paycheck. When I finally took an honest look at where my money was going and why, I knew I wouldn’t even need half of what I was making at that job if I just had the time and the space to make meals and stop buying myself things to make up for the fact that I was miserable and had no time for actual experiences.

Taking the first step

I knew my end goal was to have the time to give freelancing a fair shot, so I didn’t want to go from one shitty job to another shitty job. So, I looked for gigs instead. I started applying to job boards like UrbanSitter, SitterCity, Wag, Rover, Postmates, and Tasker. I waited, had a couple of interviews, and ended up going with a part-time nanny position for a family who found me on UrbanSitter (who have actually become some of my favorite people on the planet). At first, I did make exactly half of what I was making as a manager, so I made the very least I could afford to get by with. But, having that free time allowed me to put myself out there to design websites, do some social media management, and freelance writing, and I’ve ended up making more than my manager salary. I just had to take that first, scary step.

I do have the luxury of being in a committed relationship and having two incomes, but I would have taken the same route if I were single. It was more important to me at that point to reduce my stress and work towards my end goal of becoming my own boss than it was to have things. If I were in the same situation and single, I’d still look at my spending the same way and figure out the bare minimum that I could be happy with to bridge the gap between my shitty job and following my dream.

And if you’re in a situation where you feel stuck but you think leaving your job is too risky, think about this: my manager job was at a big, corporate chain store, which most people equate with stability, and there were massive layoffs about 8 weeks before I left and I knew I could be next. There can be just as much risk in working for someone else as there is working for yourself.

At the end of the day, time has been more valuable to me than money. And, from the extra time and mental space, I’ve been able to make more money. To me, it’s worth it. I know I’m working towards something meaningful.