Startups are fun, they said. It’s totally worth it, they said. You can make a ton of money, they said. Not quite sure who “they” are but that’s what I tell myself when I think back to when I made the decision to jump from a mid-size company with 40 years of history to a startup with 20 employees.
I had been working for 17 years in a larger company, I knew my job, made lifelong friends, but I was bored. I had the good fortune of some great managers along the way and was a Director by the time I was 33. But after working in one place that long it meant most people had known me for years, they knew me in my twenties when I was perhaps not the best version of myself. They remember your humble beginnings, when you drank too much at the holiday party, when you hooked up with that guy from another office, etc. People have long memories especially when those people are in line to promote you. The company was located in Silicon Valley, I live on the East Coast. The only way to keep climbing the proverbial corporate ladder was to move west. Considering the cost of living was so high in the Bay Area I declined and was stuck.
A few months before the pandemic started I had made the decision to start looking for a new job. I updated my resume for the first time in ten years and learned a huge lesson: update your resume at least once a year. You won’t regret it. I had applied for several jobs and started interviewing when COVID hit and I decided to hunker down where I was, especially seeing other companies starting layoffs. I worked in HR and when I tell you that the pandemic soured me on HR and frankly people in general that would be an understatement. Quickly the HR team, so often ignored and seldom with a seat at the table, were the most important team at the company and it took its toll. From putting together a work from home plan for a global company, dealing with employees getting sick and losing loved ones, to the general cabin fever that we were all having, my team and I were mentally and emotionally exhausted. While we were the ones everyone turned to, there was nowhere for us to turn except each other. I was done. In my head I thought that I was done with the company, not HR. If only I could find a place where I had my own team, was running strategy, and could feel passionate about building something from the ground up. I was ready to leave and towards the end of 2021 I had started to think about what was next for me.
In a stroke of luck or the universe aligning in my favor, a recruiter reached out to me with a job opening for a Head of HR at a local startup. The pitch read like my personal list of what I wanted in a new role and company. I was excited and scheduled a call with the CEO. We quickly hit it off and I was impressed by his commitment to people and culture and he seemed genuine. After a month of interviews an offer was made to me, I accepted, and cheerily turned in my resignation to my boss who I could not stand. I made another huge mistake and lesson number two: take time off between jobs. Unless you cannot afford the break and/or there will be a gap in health care coverage I would implore you to take the time. I did not and regret it to this day. I needed time. Time to properly grieve the loss of a company, co-workers, and a life that had been so familiar for so many years. I needed the time to just take a break and do nothing. Instead I jumped right into the deep end and hit the ground running.
Fast forward three years, two rounds of funding, and four layoffs I started to think that maybe the company wasn’t what I was desperate to leave, but maybe it is the entire career path I had set for myself. I held the title of “Head of HR” for about a year and was then promoted to VP, with a seat on the executive team. I had finally reached the top and it was lonely. Lesson number three: no one knows what they are doing. Before I left my previous company a former colleague had told me the grass isn’t always greener. I was annoyed and thought nothing could be worse than this, but I was wrong. Now, that being said, my new company is great, I accomplished pretty much everything I wanted to, there is a great culture, great morale (before all the layoffs), and I was able to build the best team that made work fun again. But there was that nagging feeling that was still there, I wasn’t jumping out of bed with excitement at the challenge ahead and frankly, while the timelines were crazy I didn’t find the work to be that difficult. What was difficult was realizing that while I knew what I needed to do, no one else did.
Once I joined the new company I quickly realized that my previous experience made me the most qualified member of the executive team. That’s startup life. Executive teams are often people who have only worked at startups and never experienced real growth or people who were good at their jobs and quickly promoted into leadership roles they were not qualified for in the least. I found myself in a position of providing strategic direction to other leaders and taking on way too much. The hours are insane and the pressure is unlike anything I have experienced. At my previous company we never had financial issues, always turned a profit, and I never had to think about where the revenue was going to come from. Fast forward to startup life, as a member of the exec team knowing how much cash is in the bank adds a level of responsibility and pressure I could not foresee.
My stress levels are at an all time high. I am not taking care of myself in any way which adds another thing to worry about on top of work. I am not sleeping and a glass of wine at the end of the day has turned into the occasional bottle when things are really bad, which is often. Just when I think I have started to move in the right direction something comes up at work and pulls me back. I often feel like I am in a rinse and repeat cycle and there is nothing I can do to get out of it. I feel stuck in one place while everyone else around me seems to be moving at lightning pace.
I started this blog because I thought I can’t be the only one who is not holding it together. No one may ever read this but it’s cheaper than a weekly therapy session. I have bi-weekly therapy in case you were wondering, it helps, but this helps too and I will continue until I don’t see value in it anymore.
If you are reading this, thanks, and I hope you find something in this blog that makes you feel less alone.
Leave a Reply