5 things I did before quitting my day job


Today I got up, got dressed, and didn’t go to the office.

After a little over a calendar year, I quit my day job at a political think tank in downtown DC. I didn’t leave any richer (and in fact will be closing out the year with my lowest earnings since starting out on my own) but I got exactly what I wanted out of this year—experience working with a development team and renewed confidence that my tech skills are still marketable.

However, this decision didn’t just happen two weeks ago when I gave my two weeks notice. I’ve been preparing to go back to full time freelance for the better part of six months.

Here is everything I did before I felt ready to quit my day job:

Contacted previous employers

While working part time, I scaled back my freelance to a smaller goal—to earn about 50% about what I earned the year previously, the better to not kill myself with overwork. That meant working less for some clients, and not working at all for others.

It’s a lot easier to pitch somebody who has previously given you money than it is to cold call a stranger. So when I knew I wanted to start freelancing again full time, I went back to the people I already knew. One of the most positive outcomes of this was when I let a client know I was looking for more work right away, and it turned out they immediately had a gig right up my alley!

I would recommend this plan of action to beginning freelancers, too: if you don’t have previous clients, try friends, family and professors. You never know which person might know another person who needs a freelancer with your particular skills.

Doubled my freelance work immediately

As a result of getting in touch with all those clients, these past two weeks have been pretty hectic. Just as I started winding things down at my day job to prepare for my exit, I started revving up the freelance engine again. Projects I might have otherwise said no to, because of the day job? They were suddenly on the table.

The entire goal is to have a steady stream of income without a break. Since freelance tends to pay out slower than the two-week regularity of an office job, that meant starting early. It meant taking on full time freelance while still doing part time work. It meant working until 1 AM a couple of nights. But now that that’s over, I don’t have to worry about empty days and an empty wallet while I scramble together a full time income post-day-job.

Saved an emergency fund

No matter how many precautions you take, freelance is still risky. (I’d argue that a regular job, which means putting all your eggs in one basket, is equally risky, but that’s just me.) If you’ve been reading my last few income reports, you know I’ve been padding an emergency fund.

In my opinion, a good emergency fund includes three month’s worth of living expenses. Being totally unemployed for three months is an unfathomably bad scenario, but I want to be prepared. I added up the cost of rent, groceries, my Internet bill, and other expenses for a month, tripled the number, and kept saving until I reached it. Ideally I will never, ever use this money, but wow do I feel a lot safer just knowing that it’s there.

Set up a daily routine

Last year around this time, I didn’t have a great freelance schedule. I slept in and as a result stayed up too late hurrying to complete the work I didn’t finish earlier. I wasn’t on the same schedule as John, who works a 9 to 5, and I didn’t see him as much as I wanted. The truth is, I was severely lacking in self-employed discipline.

I didn’t want this to happen again. So I thought about all the things I liked about my current set-up—getting up and dressed in the morning, walking to the station with John, talking to other humans on a regular basis—and thought about a routine that would let me keep that. I decided that even though I don’t have to go anywhere, I should keep getting up and dressed in the morning anyway, walk to the station with John, and just walk back after that. The brisk walk helped me ease my brain into the work day. From that morning routine, I set up a schedule of things to do until around 6 PM. To ensure I retain my social skills, I’ve got Skype and Slack with other freelancers during the day, and Japanese class and running club in the evenings.

You’d think work-life balance wouldn’t be a problem when you work from home, but tell that to my first-year-freelancing self, who used to sometimes forget to eat. Making a routine and sticking to it will keep me from regressing into lazy misery.

Made a three-month financial goal schedule

Finally, I laid out the next three months on a spreadsheet. I listed out my clients and projects and my projected earnings from each. As the real earnings come in, I put them in a third column and figure out the difference.

This offers some structure to my career. It shows where I thought I’d be at this point, where I really am, and whether I’m exceeding or falling short of what I need to make to pay my bills. If I’m right, awesome, I’ll keep doing what I’m doing. If I’m wrong, I have a wake-up call right away that I need to be doing something different and taking on more work. It also shows me how much space I have to work on new business ideas, which won’t pay off immediately, and when I’m better off devoting time to client work, which will pay off much sooner.

I was never a numbers person before I started freelancing, but now I am by necessity. Math still isn’t my favorite thing, but knowing I have numbers to back up my decisions definitely makes me feel a lot better.

Do you have any questions about going from office work to freelance work? I’ll do my best to answer them in the comments.