Between The Great Resignation and Beyoncé blessing us with the single “BREAK MY SOUL,” it seems like quitting my job of 6.5 years in May could have just been me jumping in on a current cultural trend. But in 2020, I developed a 3-year plan to slowly phase myself out of that salaried position and into self-employment. Things just did not proceed quite the way I thought they would.
Planning is necessary, though, if you’re not independently wealthy. And, of course, if you were, you probably wouldn’t be stuck in a job you hated to begin with. If you’re not rich and want to quit your job, I can tell you how I did it.
It’s important to note that I was also able to quit because of my job–that is, a well-paying job with a web development agency. Most of the time I worked there, I made $70k+ annually, a distinct advantage that allowed me to grow a savings account. I don’t believe you necessarily have to work in tech to be able to make enough money to save some of it, but I would never say that people making less than that in the US should have no problem saving the way that I did. Especially now. But, nevertheless–
Step One: Figure out what you need.
I aimed to turn my screen printing hobby into a full-fledged entrepreneurial endeavor. I needed a place to do business, a way to pay for upgraded equipment, health insurance coverage, and a way to cut down on expenses so I could continue to financially contribute to my household.
Our rent went up in 2021, exposing another underlying need: a house. We knew that a mortgage would likely be cheaper, and if we found a large enough home, I would be able to use some of the space for my business. That would mean I didn’t need to pay rent on a separate studio.
Plus, once I quit, we would no longer have the credentials a bank looks for in doling out home loans. We needed to put this element of the plan into place first.
Step Two: Figure out how to get it–and execute.
My partner and I had been engaged for a couple of years, so we decided to get married in a backyard ceremony in late 2020. Then, during health insurance open enrollment in 2021, I signed up for health insurance as a dependent of my spouse in preparation for my departure.
One of the first things we did after our wedding was open a joint high-interest savings account. It offered 1% interest (now 1.25%), so we put as much money into that account as possible. We were able to put away at least a few hundred dollars every month after the bills were paid.
With this aggressive savings approach and the interest rate, by October 2021, we had a little over $15,000 saved. We’d spent that summer and most of the fall looking for a house, attending 2-5 open houses every weekend like we had second jobs.
When we finally found our house, the price was at the top of our budget, and we needed to drain our precious savings almost completely. We both grew up well under the poverty line and had never experienced having that much money before. We were reluctant and terrified to let most of it go, especially knowing I planned to quit my job in a little over 2 years–but the house was a crucial part of that plan. So we convinced ourselves to move forward and were homeowners by December.
With that done and our living expenses lowered and stabilized, we resumed socking away as much money as possible into that savings account. I thought I had a while to do that and use some of that money to help pay for the equipment I needed.
Step Three: Pursue your new future.
I forecasted my last day as January 18, 2023, because that would mark my 7th work anniversary with the company, which felt like a very tidy way to leave.
In 2021 I began looking for my replacement at my salaried job. I figured I could train this person in everything I did before I left, and I started stepping back from some additional responsibilities I had been given.
Then, in January 2022, a mutual acquaintance introduced me to the state’s LGBTQ Chamber of Commerce director. This chapter was running a program for start-up businesses. It assigned participants to a business coach, a lawyer, an accountant, and marketing specialists; it also provided opportunities for grants, like one to create/recreate an e-Commerce website. I applied for this program and was accepted.
In March, I decided on a whim to look for a conference I could attend for screen printing. I had only ever participated in tech conferences for my salaried job, which were usually dull and attended by people I had nothing in common with.
I had incredible, validating experiences at the screen printing expo. It was thrilling to feel knowledgeable about and experienced in a topic I loved so much. And I was indirectly reassured in every workshop, talk session, or training that successful apparel decorators are organized, process-oriented people–just like me.
Step Four: Be prepared for anything.
Back at my salaried job, I had increasingly frustrating discussions with the company owners. This was not atypical. In fact, many of the conversations revolved around topics I had been pursuing my entire tenure with the company. But returning to work after the printing expo felt like the textbook definition of “night and day.”
It was suddenly obvious to me that I could not last until January 2023.
As I got more vocal about my disagreement and discomfort with the direction the company was pursuing, my work environment was growing more hostile. But it felt like something inside me had been ripped open and I couldn’t close it again–I could no longer pretend to care what these weird Libertarian Elon Musk fanboys thought.
Leaving my job early meant losing several months of income, tens of thousands of dollars. So I knew if I was going to do this I needed an emergency backup plan to recover some of that money. And here’s where I have to warn you to proceed at your own risk because… really, all I had was my intuition.
Step Five: When necessary, make a new plan to get what you need.
I had many years with this company and held a leadership position, so please understand this was a bit of a calculated risk.
I went to my direct supervisor and told him I couldn’t do it anymore. We had similar ideas about the company; he knew I was getting sick of the games, so he wasn’t shocked. I told him I was ready to be done that day but could give him two weeks. He sat up straighter and muttered something about his vacation the following month, so I said:
“I will stay for two months to ensure a smooth transition to my replacement in exchange for a severance payment.”
When we reconvened following his discussion with the company owners, I did get a shock:
They. Agreed.
The severance agreement I signed when I left prohibits me from disclosing the agreement's details or the payment I received. But the payment was made to the LLC I established for my new business, providing me with enough funding for new equipment. With my spouse still secure in their salaried job and able to save money, all the pieces were as in place as they could get.
Step Six: Don’t look back.
I went full steam ahead. I formally gave notice and began the process of converting my basement into a print studio. I ordered new machinery and started working on a new website. I got a certificate from the state that allows me to legally sell things. I was a business owner in what felt like the blink of an eye.
My last day in my salaried position was May 31, 2022, and I haven’t received a paycheck since mid-June. Everything feels amazing and wondrous, with a current of terror running through it.
Am I making boatloads of money? No, not at all, I’m definitely losing it. Am I worried about our savings running out, my spouse losing their job, or what will happen when my business funding is spent? Yes, definitely.
But every day I can wake up now and get right out of bed. I’m no longer moaning to myself, “What’s the point?” as I send my 12th, 30th, or 51st email of the day. I have nothing to prove to greedy businessmen. I’m doing work I love to do, on my own schedule, and my point is to feel happy and fulfilled.
Even if I can’t enjoy this forever, I am grateful for every minute that I have right now. No amount of failure on my own is going to feel as bad as trying to succeed for people who would never acknowledge my work.
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