I’m 37 and this is the last 9-to-5 I’ll ever have

Cookie's Corner
8 min readNov 30, 2022

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As a child I always wanted to wear the nice suit and designer heels to my fancy job in the city with my cute corner office. I got the nice salary, outfits and office at the age of 30 and now years later and post-quarantine I will never look at my career the same way again.

Photo by Georgia de Lotz on Unsplash

It was an easy road until I had to find my first job. As a woman of color in an urban area I was fortunate enough to attend private school my entire life. Good grades and athleticism came naturally to me. I got my degree from a top 30 university without having to attend every single class and hardly pulled all-nighters. I could have worked harder but I was an early adopter of working smarter instead. I appreciated what little privilege I had and knew that these accolades were my defense in a world that placed human worth primarily on the color of one’s skin. While all of my accomplishments made me “elite” on paper, the real world had other plans for me post-college.

I had my first child during my senior year of college. So naturally I was on a mission to start making money as soon as I graduated. I worked a few temp jobs that summer, always being told that companies wished they had had the opportunity to hire me (many temp agencies at the time restricted companies from making offers to employees). While that was flattering the roles were ultimately not ideal and I also wondered what all of these companies’ recruiters were doing since my resume was posted on every job board known to man. I finally got a part-time job at a bank until I could convince my manager to make me full-time. That manager was my only advocate and when she moved on to a corporate role at the same company it was bittersweet. As soon as I got pregnant with my second child I began applying for the loftier corporate roles too. I didn’t even get a first round interview. Soon enough I was out of time and had to transfer to another more affordable city to work and live.

The next best job I could find was another entry-level role making $12/hour. I was hired as part of a group of 12 people into a new department. The team went through multiple rounds of layoffs within the next 2 years and one promotion later I was one of two people left. It was a hostile work environment the entire time. From people making fun of others’ accents, physical characteristics and suggested sexual preferences to others’ loud and proud declarations of political preferences and wilderness hobbies I thought I’d tough it out and focus on the work. In the meantime I enrolled in an online MBA program and when my toddlers went to sleep I studied. As my program winded down I began applying for roles at companies where I had hoped the grass would be greener.

I probably submitted at least 100 applications each month. I had about 5 interviews total. I remember showing up to one where the interviewer and I both realized about 5 minutes in that I was not qualified for the job. The hiring manager was very gracious about it but how I ended up there to begin with I’ll never know. I just knew that I was hungry and had mouths to feed and would never pass on any and every opportunity. Sprinkle in constant rejection with humiliation at the county office to get government help and desperate cannot even describe how I felt as time passed.

In true universe fashion, I finally got a call from a Fortune 500 company. It was not for a job to which I had actually applied but instead a management trainee program. It would last 9 months and I would not be guaranteed a permanent role at the end but it paid $5 more per hour than I was making and it was a respectable company to add to my resume no matter what. After a few interview rounds and a worrisome background check (my credit was horrible at the time) I was ready to move on to my next opportunity.

Working for a large corporation met every expectation I had and then some. I finally had an excuse to run up a credit card to get the business clothes my 12 year old heart desired. I could make my peers and ancestors proud having expanded into this new territory. It was time to kick ass and carry the torch for others who looked like me. I never questioned why this program seemed to be the only way for women of color to get hired or why the men in the group who were not diverse at all got promoted faster post-completion. By the end of the program I got offered a role that paid substantially more (still less than market value though) and that’s all that mattered. Nevermind the misogynistic manager I had, I was going to do my minimum time required in that role and then put myself in a position to get promoted. I became immune to the anxiety the constant questions about why I was so quiet or lacked “passion” or where I was from created and continued to let my unparalleled work speak for itself.

At some point amongst the promotions I became jaded. But really I reached a glass ceiling of sorts without realizing it. Possibly because it was seemingly lower that the ones I saw other women encounter — but it was still there for many nonetheless. How could I expect anyone to reach down and help me when they are clinging to their own ladder? I kept hope alive though and attempted to network despite the many subtle rejections I encountered. Whether it was someone forgetting my name or accomplishments, I did not hesitate to remind them of who I was. The Kool-Aid went sour. Then the projects dried up and I began to wither away in my 3rd floor office until a new opportunity came along.

The new role seemed more lucrative, and it was from a salary and travel standpoint. I quickly learned that perks were a distraction from the inability to make lasting positive change. At its core the company was dysfunctional, and the similarities between this place and my last companies hit me like a ton of bricks. I’ll never forget the last straw: My manager repeatedly asked me to host a workshop that I felt wasn’t necessary at the time, as many people were already stretched thin working on another massive project and I preferred to let my team divide and conquer in order to give our most difficult peers the time and attention (mainly flattery) that many of them inexplicably required to thrive. I caved in as many good employees do and hosted a meeting. When it came time to do a group activity critical to completing the workshop my archnemesis refused in front of the entire conference room. Nobody had my back. Not even my “leader” who assured he would help when things went sideways. Couple this with the strange chemistry/tension we shared most of time working there and I resigned that afternoon, just after ending the workshop way ahead of schedule.

This was December of 2019.

I waited a month to file unemployment, mainly because I didn’t know you couldn’t get back pay. I started making food deliveries to make ends meet while I explored the startup and venture capital world that had always fascinated me. But I couldn’t help but notice that many of the faces I encountered in these circles looked the same, and hardly any looked like me. I soon realized that I didn’t have the capital or connections to make a leap into my own venture just yet. Defeated, I took a contract role for less money that a friend of a person I hired at a previous company helped me get. In fact, many of the people I have hired or managed are just a call away and one of the things I most appreciate about all of this is that I can still help them develop their careers. For me though, before I stepped into this role I knew that this had to be the last corporation for which I’d ever work in this capacity. It’s nothing personal, I have witnessed too much in good conscience to ever believe that a company would my back, especially compared to all of the people in its highest ranks. My contract kept getting extended and after false promises of a permanent leadership role that went away because my CRO thought I lacked passion and didn’t speak loud enough (a comment that only seems to come from the same type of person) an even higher level role in an area where I was more familiar opened up. I was promoted into a permanent executive role about a year later.

A quarantine promotion as I later learned, were hard to come by. I did not get any busier than before. In fact, I found myself with more free time and a sense of loneliness at home that I initially hated. Turns out I now had proof that I could be just as if not more effective with four hours from home compared to the 8+ hours each day in office. Despite making $5K more than I ever have before I still found myself unfulfilled and over the corporate nonsense. As the events of 2021 unfolded I decided to bring one of my personal passions to work and begin spearheading DEI efforts at my organization in addition to my regular duties. I thought this would help me find my motivation to look forward to work each day. The red tape and bureaucracy I ended up facing did quite the opposite. I push forward as I remember that a 12 year old out there who looks like me might want to be just like me one day, and perhaps they will love the corporate thrill of it all and surpass where I’ve landed. So you will continue to see me accept the many council, interview and panel invitations I receive as a thought leader in my industry but it is only to keep hope alive for the dreamers out there.

Today I use my free-time to do gig work and pursue personal interests. I guess I was quietly quitting before it was a thing. I feel like boundaries is a more accurate description though. With the state of the economy and my sub market value salary I have had to go back to gig work. This time around however I enjoy the ability to make money on demand and on a flexible schedule. Then there’s my podcast, an un-related IG and You-Tube channel, Twitch streaming that my significant other has brought me into, Amazon affiliate and self-publishing efforts — and this neglected blog. My younger self would not believe me if I told her that the fancy job she always wanted would never live up to expectations, but I hope I can one day show her the pricelessness of pursuing personal passions instead.

If you like my content and want to say thanks you can buy me a cup of coffee! It is not expected but greatly appreciated. Happy holidays!

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