Differently Employed: Lessons a Year After Quitting the 9 to 5

Last June I quit my 9 to 5 job and didn’t know quite what to expect. I’ve stumbled along the way, drifting in and out of the different income streams. Where I started is not where I am now, and I wanted to share about my journey of being “differently employed.”

Lesson 1: It’s OK to Change Your Mind

When I first started working for myself, I wanted to blog full-time. Shortly after I realized it wasn’t for me for a lot of reasons, but mostly because it wasn’t simulating, exciting or interactive enough. It essentially amounted to me sitting at my desk. A lot.

I don’t want to neglect the importance of money, so I want to be honest that blogging didn’t bring in a ton of income. Those Graces isn’t set up to make money because I thought it was too personal to be an advertising avenue. Realizing this, I relaunched my beauty blog, which felt more monetizable. But then I realized I didn’t really like writing about makeup, so Beauty Shy closed. (RIP)

After these challenges, I realized full-time blogging wasn’t quite for me, but that doesn’t mean it’s not part of my career strategy. It’s just a smaller part.

Lesson 2: Find a Career Counselor

One of the best things I did was to go to a career counselor. (If you’re in the Boston area, Phyllis Stein is amazing!) Quitting my job confused me in ways I didn’t anticipate. What should I do every day? What was a good at? And, most importantly, what did I really want to do? These are all questions I could’ve answered by myself, but it was so helpful to have someone to guide me along the way.

Not only that, but career counseling taught me that failure was OK. When I was having mixed feelings about blogging, I looked at it as a failure, whereas my career counselor encouraged me to look at as a learning the lesson. I was grateful I realized within three months that full-time blogging wasn’t for me because it allowed me to invest my energy elsewhere.

Lesson 3: Choose Your Clients Wisely

If you’re freelancing, you’ll likely working with various clients. Choose them wisely because they’re mini-bosses. If your project has an end date, maybe it doesn’t matter that your client is a micro-manager, but if it’s long-term, you’ll want to consider how well you click with them. This isn’t to say if the project isn’t going well that you can’t end it, but it makes it a lot easier if it goes well from the beginning.

Lesson 4: Set Some Sort of Schedule

It makes me feel good to have an idea of what I’m doing every day, even if it varies. In the mornings, I typically take time for myself by walking to go get coffee or exercising. After lunch, I usually work on whatever’s going on for Overdressed Me, whether it’s shipping items or putting up new listings in my shop. Usually by 2, I’m working on freelance projects until 6:30 or so. Then at night, I hang out with my boyfriend, run errands and go to events. Later at night, say from 11 until 2, I’m working on Overdressed Me.

Working late doesn’t work for everyone, which is why I think it’s important to experiment with different schedules. Don’t be afraid to switch it up. Some days I like to stay up working until 2 or 3 in the morning. Others I prefer to go to bed around 11 and wake up around 8. It all depends on what I’m feeling and when I feel most productive.

Lesson 5: Make Sure You Get Out of the House

The most challenging thing for me about working from home was the lack of daily socialization. I’m very talkative and genuinely love interacting with others. For me, the decrease in the number of people I saw every day was the hardest part about working for myself. To deal with this, I make sure I go to various meetups, hang out with friends and get outside. Though I definitely see less people, I feel like my interactions now are more meaningful and deeper than they used to be.

So those are my lessons after a year of quitting my 9 to 5! Would you ever work for yourself?

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