Before my nine year stint at Corporate, I had a whole lot of confidence for someone who hadn’t really proven herself yet. I was fresh out of college and working a 9-to-5 I didn’t love when I decided I was going to throw the largest Menstrual Hygiene Day event in the country. No experience, no permission—just an idea and a notebook full of plans.
Not long after, I ended up at a concert standing behind Emily Evans, the Executive Director of the Women’s Foundation of Oregon and someone I really looked up to. So I tapped her on the shoulder. When she asked what I did, I didn’t tell her about my day job—I told her I was launching PDX Red Party, the country’s largest Menstrual Hygiene Day celebration (at the time), and asked if the Foundation would come as a vendor. She said yes, and a few months later, I was watching 150 strangers play period-themed carnival games in downtown Portland.
That same confidence carried me across the country to Chicago, where I signed a lease on an apartment sight unseen. I knew literally one single person in the city (hi, Jen!), and my friends, family, and loose acquaintances all had so many questions about what my life would be like in such a big city, so far away from home. I didn’t know the answers to most of the questions, but I knew that I could and I would figure it out. So I hopped on an airplane with a suitcase full of clothes, a suitcase full of books, my tiny dog, and an unwavering belief in myself.
Because everything was so aggressively brand new to me, I intentionally decided to keep my job as an anchor of stability while I got acclimated to my life in Chicago. My intent was to build up my network for a year or two and then to change jobs to something local.
But soon after I started dusting off my resume and applying for jobs, the world started to shut down as we entered a global pandemic. I was there, you were there, I know we all have our scars, so I won’t rehash that here, but suddenly, changing jobs didn’t seem like the best idea anymore.
A few months later, I got pregnant and then it really didn’t seem like a good idea to leave a job with solid maternity leave benefits.
When I got back from maternity leave, I was offered a leadership position I had been pining after since I started at Corporate, so I stayed and I built a team from the ground up. I loved every minute—watching my team growing in confidence and competence, becoming increasingly independent at a similar rate to that of my child.
What’s that Green Day lyric again?
Time grabs you by the wrist, directs you where to go.
It was around this time my view of my career changed pretty dramatically. I was a young leader who had gone from intern to manager fast, and I led a young team. Somewhere along the way, I got the sense that I wasn’t being taken as seriously because of it.
Instead of shrugging it off, I took it as a challenge and fixated on proving myself to my fellow leaders, surrendering to this deep, almost maddening need for others to see my competence as I saw it myself.
I leaned into the corporate climbing. The schmoozing, the rubbing elbows. I started making long-term plans, envisioning the evolution of my role in years instead of months or something smaller, and viewing my career and my Corporate trajectory as one and the same.
That’s when it stopped being a job and felt more like a marriage.
Like any marriage, it asked for a little more of me over time, and I kept saying yes. Work got the best hours and the sharpest part of my attention, and slowly everything that wasn’t work or my daughter got trimmed away to make room.
Friendships thinned into texts I meant to answer and didn’t. I stopped going to things. I even stopped grocery shopping in person in favor of Instacart and other delivery apps, so every spare minute could go to my daughter and every other minute could go to my desk. In no time at all, I was burnt out, and so far up the corporate ladder I could no longer see that 22 year old girl who’d tapped a stranger on the shoulder and declared herself the founder of an event that didn’t exist yet.
And then Corporate broke my heart.
When you’ve built a whole life with someone, you can’t just grab your keys and go. There’s the lease in both your names, the furniture you picked out together, the friends you’ll have to divide. The months it takes to find a place that’s only yours. Deciding to leave is a single moment—disentangling is the work.
I needed to do the professional version of that.
My professional network, examples of my work and skills, my competency and authority all only existed inside of the four virtual walls of the zoom rooms of my organization. I had not spent any time thinking about what I would do next, and I didn’t have any idea as to how to begin translating any of the work I had done into a new context.
The very first thing I did to change things was sign up for a coworking space. I am a huge champion of remote work. There are so many benefits to working remotely for individuals, teams, and companies alike. But I also know it is imperative that you expand your network in real life—to have an excuse to put on hard pants and get out of your house once or twice outside of weekend plans.
I ended up chatting with the owner for a full hour after touring the space. She asked about my work, about my leadership philosophy, and the conversation was so cup filling, so easy and fun. I felt a little flicker in my soul that I hadn’t experienced in too many years. I have always been good with people. I love to talk and I notice that people seem to enjoy talking with me too. It felt so good to flex that muscle and I felt almost embarrassed that I had let that part of me go dormant for so many years while I chained myself to my desk most days.
Next, I reached out to two of my very good friends who were just beginning their own career transition journeys and set up weekly accountability calls with them. I’ve known these two women for an entire decade and they are two of my most trusted, most respected confidants. They know my working self better than almost anyone—my ambitions, my blind spots, the whole unedited picture—and, over ten years, became some of my dearest friends. So, while we were all in the thick of figuring out our next chapters, I knew we would all be better served to work through some of that together.
Then I started reaching out to people who knew me before I started working at Corporate, before my life in Chicago. And even though I hadn’t done a good job staying in touch and keeping up with any of them, I was delighted to find they all said yes.
These conversations turned that flicker into a flame inside of me. Each call, each conversation was like an opportunity to see myself reflected back to me outside of the org chart, outside the four walls of those zoom rooms.
In the midst of this journey to re-expand my world and find myself outside of Corporate, I randomly opened one of my graduate school program newsletters. I hadn’t opened a newsletter in years, and I was excited to see one of my cohort members, Antha, was the alumni feature—talking about how she was using skills and learnings from the program in her new business Late Breakfast, focused on, of all things, burnout recovery.
I DM’d her and asked to chat.
Like me, Antha had been in her own LTR with a company, having worked there for eight years when she finally took the plunge and left her job to start her own business. I expected her to tell me how much her work-life balance and her mental health improved when she quit, but instead she told me how her burnout worsened when she set out on her own. She said the bad habits that led her to burnout in the first place followed her into her business and that in some ways it was even harder to break them because of the pressure of being a solopreneur.
I remember saying to her on the call, “shit, I think I would do that.”
Some lessons don’t need to be learned the hard way. So, I chose to stay (for a while, anyway—I did eventually leave), but I was no longer in it to prove myself to anyone but me. I put the job on a good-enough autopilot and spent my real energy elsewhere: setting boundaries around my calendar, taking breaks to eat and move my body, flexing muscles I’d let go stiff.
I realized I’d outsourced my self-worth to performance reviews and the approval of leaders I didn’t even respect. At 22 I’d had all the nerve and none of the evidence; by the time Corporate broke my heart, I had the evidence and almost none of the nerve.
One conversation at a time, I got my nerve back.
I remembered my career was never my job title or my place of employment. It’s so much bigger than that. It’s mine.
It turns out that’s a dangerous thing to remember. Because a woman with the nerve and the evidence doesn’t stay on autopilot for long.
She starts building.
(But that’s the next story.)
So, that’s a wrap, friends. If you feel this was time well spent, give this a little heart or leave a comment below. If you think you might want to spend more time with me each week, subscribe to Time Spent.
I’m Tiffany—a multipassionate mom, living in Chicago. I spent the last decade climbing the corporate career ladder, but now I’m officially off the clock and spending my time on the things that light me up the most. Like writing this newsletter. You can learn more about me by visiting my Substack homepage or by visiting my website.
Bye for now.
