6 Lessons from My First Month of Self-Employment

Photo by John Schlia Photography

Photo by John Schlia Photography

Today I’m celebrating. Why? It marks the one month anniversary of me leaving my full-time job to pursue the great adventure of self-employment. No regrets so far! I’m trying not to let myself wear rose-colored glasses all the time; working for yourself can be lovely, but I know it won’t always be easy.

I’ve learned a lot in the first month (and I know there’s more to learn ahead!). To celebrate the one month milestone, I’m sharing a few of the lessons I’ve learned so far.

1) Carve out time to do the work

Coffee meetings are fun! I’ve met so many interesting people and had lots of great conversations since leaving my day job. I’ve cranked out 10 proposals for prospective clients in the first month alone. But woah, when do you actually sit down and do the work?

Many days, I’ve found myself sitting down at my desk at 3pm, utterly exhausted after running around to several different meetings. I walk a fine line between introversion and extroversion, so the meetings can be both energizing and draining.

So far, I’ve carved out Mondays as my meeting-free day. That’s when I plan to dive in deep and do the work. I’m also trying to set some rules for myself, like no more than one meeting a day (though that one may not be feasible). I need to find balance and figure out what works for me. I’m still getting there!

2) I’m the boss.

Freelancing full-time has not been 100% stress-free! When I feel stress starting to creep in, I have a tendency to yell at myself: “You’re the boss! If you’re stressed, you must be doing something wrong. Did you set an unrealistic deadline? What did you do wrong?”

I’m trying to remind myself that me being the boss is a good thing. And I should be nice to myself, as my own employee! In these moments of stress, I’m striving to step back and analyze why the stress is coming up and what I can do better. But at the same time, I’m also aiming to give myself space and time to grow and adapt to this new work life I’ve got.


3) Invest in developing processes

Process matters. I can feel myself getting more efficient every day! I started using Zoom for all of my meetings, which has worked very well. It’s great for scheduling, sharing screens, and taking calls right on my computer. I also signed up for a Google Voice number, which has been helpful for those “hey, shoot me your cell phone number so I can text you if I can’t find you in the coffee shop” moments where you don’t want to give out your personal cell.

I’m still working on getting my workspace just right. Today I’m trying out a new monitor, keyboard, and mouse situation. I think I like it, but I’m still adjusting. I may invest in a laptop stand soon.

Other things I can’t live without: Google Drive (it’s where I store everything and what I use for putting together client proposals), the new “schedule send” feature in Gmail (essential for drafting an email response now but sending it out a little bit later, so people don’t get the impression that you’re always available), and QuickBooks (which has been awesome for tracking expenses, and I’m just starting to use for invoicing).

Though it does take awhile to get all this set up at first, I know it will be worth it in the long run! So many time savers.

4) Confidence is key

I think just about everyone under the sun has dealt with imposter syndrome at some point in their life. It creeps in from time to time for me. Sometimes, I’ll be working on a social media strategy for a client and I’ll think to myself, “This is all so obvious. Why are they paying me for this?”

And then I remember: it’s not obvious to everyone. I’m an expert, and that’s why they hired me.

Then I’ll present the strategy to the client and get reactions along the lines of, “I never thought of that! What a great idea! Thank you so much.”

Presenting yourself with confidence is key, though it’s much easier said than done.

5) Listen to your gut

I’m starting to get better at this one. Sometimes, you have a gut feeling about a potential client or opportunity. It just doesn’t feel right. You can’t identify precisely why, but a voice within you is telling you it’s not a good fit.

Listen to it.

We have intuition for a reason. I’m trying to pay more attention to mine, and not fall into the feast/famine mentality that’s so common among freelancers. It would be easy to say, “I should take this project because I need money.” Saying no to projects that aren’t a good fit is the best way to make room for projects that are a good fit.

6) Take advantage of the flexibility

One of the reasons I decided to pursue self-employment was because I craved flexibility. I didn’t want to be chained to a desk from 9am-5pm. So why does guilt sneak its way into my brain when I take advantage of the flexibility I’ve chosen?

I’m reminding myself that I'm the boss. I’m going to 4:30pm cycling classes, walking the dogs in the middle of the day, and taking the occasional mid-afternoon break to read a book in the sunshine and decompress from a phone call. And that’s okay. I’m allowed. I’m the boss, and I’m going to take advantage of this new, flexible lifestyle.


Do you have big lessons you’ve learned as a freelancer or self-employed person? Share them with me on Twitter! Just tweet me at
@servemethesky.