When I was a teenager, I thought a steady job with benefits, a car, and getting the hell out of my mom’s house was the highest form of living.
Now I’m in my early thirties, turning down work regularly, couldn’t dream of owning a car, and try to spend as much time as I can with my parents when I’m around.
I grew up poor, the youngest of three boys born to a single mother who, at the time, was living in the housing projects of Chicago. At-risk youth intervention programs, sports teams, and scholarships kept me safe and out of trouble. They also built within me an eagerness to please, a willingness to accept the authority of anyone who’d buy me lunch. This served me well early in my career; who doesn’t love unblinking loyalty and a can-do attitude? I rose quickly. I took on challenges no one else would. I conquered them through stubbornness, elbow grease, and moxie.
I looked up though a couple years ago and realized that I was stuck: my wages were stagnant and the work that I loved to do originally filled me with dread. I was still working hard and had a great title and salary, but I wasn’t happy.
I would leave the house when it was dark and come home when it was dark. My phone buzzed at all hours. Company attrition changed my work life to where I didn’t quite know what my job was, or if I was doing it correctly.
Something had to change. I applied for all of the jobs. I applied for jobs I wanted and jobs I thought would hold me over for a bit. I went on dozens of interviews, but nothing stuck. I couldn’t buy a job. Then something happened: I gave up.
One day I checked into my regular meeting with my boss and, as a surprise to the both of us, I tendered my resignation, effective a couple months in the future. I’d expressed my displeasure with my role and responsibilities a couple times at that point and we’d tried different workarounds and nothing really worked. I told my boss I didn’t have a next thing lined up and that I’d happily help find and coach my replacement, but I had to get out.
I went to it. I finished at my job, took a month off for the holidays, pulled a little money from my savings to tide me over, and sent out emails saying that I was open for work.
And I fell flat on my face.
In my first self-employed month I earned a whopping $250. The second month, a bit more. By the third I was able to pay my rent. Things picked up from there though - otherwise I wouldn’t be telling this story - and I started getting close to earning my old salary just through contract work. Over time, a job that’d turned me down offered me a contract, I started taking over for workers on leave and sabbatical, and I had a project that doubled my salary in the months I took it.
I was thriving! And I was miserable again.
I was drowning in paperwork, conference calls, and some of the same tasks I’d hated at previous jobs, except I was on much tighter deadlines and I didn’t have benefits. I’d started making good money, but I was no more free than I had been when I left my job.
So I quit again.
While I was filled with gratitude to be able to pay my bills, I set out to work for myself because I wanted more freedom, not less. I wanted to be able to spend time with my family and have discretionary time for my hobbies. I wanted my time focused on work with organizations that centered marginalized folk, mainly but not limited to black men and boys. I also wanted to expand into fields that were somewhat tangential to my work and challenge myself to learn new skills.
That eagerness to please still shone through and I was worried that maybe I’d get labeled entitled, unreasonable, or difficult, and I wouldn’t be able to get future work if I advocated for my needs. I worried that I’d skunk my relationships with people who referred me to projects and that they’d turn on me. I also worried that I wasn’t good enough at my work to ask for anything and that I should take what I get. I’d already quit a decent job, this could potentially be pretty bad financially, professionally, and spiritually if I couldn’t find a way to make this work.
I got real with myself though and identified what I needed to earn in order to meet my financial needs. Starting from that point, I thought about what work I could afford to lose. I went to my clients and, as a surprise to both of us, I said no to some things. I leveraged our positive experiences and advocated for the work style that I felt I needed. I wouldn’t work on Sundays, too early or too late, I wouldn’t join every conference call, and I’d happily refer some tasks to someone else to complete. I created some boundaries for myself.
I’ve missed out on some work from some clients, but I’ve strengthened my relationships with others. By saying no to what I don’t want, I’ve had more space to say yes enthusiastically to work that I enjoy.
In my life I’ve learned that after the Instagram photos, titles, and salaries, you’ve only got yourself. You have to make the best choices for your family and your values. Sometimes that means that you have to take care of yourself first. Other times that means you can’t care for anyone else at all, or that you have to say no to people and opportunities you like.
As I’ve advanced further in my career, my ability to see the whole board has become far more important than my tactical skills. There are a lot of articles and books out there that tell you when you should branch out on your own, how to live a 4-hour work week, and things like that. My experience is that when you’re clear-headed about who you are, what you can offer (and who should want it), and what you want from your working hours, everything just works better.
Harold Moore is a Chicagoan who helps advocacy organizations including the American Heart Association, Wellstone Action, the League of Conservation Voters scale their social change efforts through tools, training, and relationships. If you’d like to chat, you can send him an email.