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5 Things I Wish I Had Done Before Quitting My Full-Time Job

I used to work at a think tank in D.C. with a guy who would say every single time I asked him how he was, “Living the dream. Living the dream.” It was never obvious if he was being sarcastic or not. But he got paid more than me, so I believed him.

Then I quit that job right after I got married. It wasn’t my passion. I wanted to write. And the experience of quitting taught me that everything looks better from the outside.

It sounds so romantic: I quit the day job that I had worked at for 6 years to pursue writing. What a dream. I took the risk I have heard countless people crave — leaving the office gig to pursue their passion work.

But if my end-goal to “pursue writing” sounds vague, that’s because it was. I didn’t have a solid plan after my 9–5 disappeared. Do I regret quitting? Abso-frigging-lutely not. It was the right choice.


There is a caveat. Everyone said it would be hard, and I knew it would be. But it was so much harder than I ever could have anticipated in some surprising ways. Certain things were easier than I expected, like adjusting to not seeing my co-workers every day. I like being alone, so this wasn’t terrible.

But for other aspects, I learned lessons the hard way. Hopefully sharing them with you will help you to avoid these growing pains.

If I could do it over again, I would:

Write Down a Risk List

In his book Quitter: Closing the Gap Between Your Day Job & Your Dream Job, Jon Acuff gives great advice about how to prepare for the leap.

He says to sit down alone or with your significant other and write down the following in a list: The risks you are taking, what you will do to prevent them, and what your response will be if they do happen.

For example: “We are risking that we will run low on money and feel stressed about it. We’ll start saving extra money now to give us a cushion. If we need to, we’ll use this extra savings for day-to-day expenses until we get back on our feet.”

Did I read this book before I quit? Nope. But that’s life. My husband and I didn’t do this, but man, I wish we had.

If we had had a written plan to refer back to when times got tough, it would have helped us immensely. A risk list is a present to your future self. It gives you back a little control when everything seems to be spinning wildly.

Build My Freelance Business Before Quitting

I would have put the infrastructure for my freelancing business in place before I quit. My freelancer website took so much longer than I expected to get up and running.

I spent weeks putting together a freelancing website, creating an online portfolio, and editing my social media accounts to reflect my new role. Did I have to do all of this before I started pitching? No, I didn’t (which I also wish I had known earlier).

But I would have to do it eventually, and if I had had the foundation of my business ready to go before I quit my full-time job, I would have felt infinitely more secure.

The experience would have been less like flinging myself off a cliff into a dark abyss and more like jumping from the high dive into a deep pool. Even if I belly-flopped, I would know where I was headed.

Prepare to Work From Home

As I said, I enjoy being alone, so I thought working from home would be manageable for me. And it was, in some ways. I already had a little office with a desk and a view.

What I struggled with was time management. Setting a schedule. Sticking to that schedule. I was good about getting up, making breakfast, and putting on clothes. What I did not excel at was staying on a writing schedule.

I avoided my desk for the first few weeks because I didn’t know what the heck I was going to write. (This stems from the fact that I didn’t have my freelance business in place before.) I had no direction in my writing.

Maybe being directionless for a while is part of the creative process. But I think it was just a way to torture myself.

I would have spent a lot of time looking at other work-from-home success models. How other writers managed their time. How they motivated themselves. That sort of thing. Then I would have felt more confident knowing I could do it, too.

Save More Money

Because my husband would continue making a good salary, we approached my joblessness with a “we’ll figure it out” attitude. Not exactly helpful for the stress levels.

Not to mention, we were newlyweds and recovering from wedding planning burnout, so we were experiencing a lot of transition already.

If we had written a risk list, we would have realized we needed to take steps before the risk started to mitigate its worst effects. In other words, we would have saved more moolah.

Yes, we had been saving for a wedding and a honeymoon. But we could have figured out a way to set aside a pocket of funds for this as well. Or at least planned to use some of the savings we already had to reduce our anxiety.

Nail Down a Solid Exercise Routine

For some reason, I thought that because I would have all the time in the world after I quit my job, I would suddenly become Usain Bolt. I would run every morning. Maybe even every afternoon, too.

Was I running much before I quit my job? Not really.

I was delusional to think that because I was less busy, I would naturally become super excited about running. In fact, in a lot of ways, having less of a schedule makes it harder to motivate yourself to do much of anything.

I’m slowly building up a solid exercise routine again, but it’s been 10 months since I quit my job. It didn’t happen overnight.

Hindsight is 20/20. Feel free to use my hard-earned hindsight to make your own transition smoother.

I learned a lot through this process, but I also could have learned things while having fewer panic attacks. But maybe that’s what it took for me to be able to say I’m “living the dream.”


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