Mid-Career Crisis? Or, a Mid-Career Awakening?

Six months ago, I resigned from my job.

It was the classic case of “easier said than done,” but I knew the work was no longer serving me, and I had to make the hard decision for myself. I’ve been at this crossroad before in my career; when I called my dad to let him know, he responded with, “You quit your high-profile, high-paying job, and you don’t have anything lined up?”....“Yes dad, I did.”

Tell Me about Yourself

When someone asks you, “Tell me about yourself,” do you start with what you do for work, or do you start with who you are as a person? For as long as I can remember, work has always been an interesting part of my identity, if not my entire identity. I deeply connected to the work I was doing, because I was proud of what I did but also because I truly believed it was the only thing I was good at. When I started working and began to see success in my work, it was like a dopamine hit. Job after job, promotion after promotion, I was addicted to being a high achiever which—as you can imagine—caused me to throw every ounce of myself into my career.

Having spent my entire career in startups, the Silicon Valley narrative always centres on entrepreneurial protagonists in their teams who are leaving it all on the line, sleeping in their offices, war hero's who are one predestined step away from changing the world. I was one of them, and then I had an epiphany—or a mid-career crisis, whatever you want to call it—that completely change my mindset.

So, what exactly happened?

I’m sharing my experience in the hopes it might help someone else in their career—whether it someone who’s also at a crossroads or someone who’s just feeling lost. If you take one thing away from this, I hope it’s to challenge yourself to think about what truly makes you happy and if you’re where you want to be. Throughout this post, I share some of the (very rudimentary) frameworks and resources? I found and developed along my course that might be an aid to you in this journey.

With that, let's dive in!?

The Breaking Point

It was the middle of May, and my partner and I were on our first vacation in over a year since starting my new role. I pre-planned everything I could. I made sure the team had what they needed two to three months in advance. Everything was set…or so I thought.

One week before my vacation one of my team members let me know they were resigning. I was devastated, but at the same time I was extremely happy for them, because I knew it was a career move they always wanted. The first day of my vacation, I received a notification from my Board Director that my other employee had given their notice. I wouldn’t even see them before I came back.?

This was my breaking point.

For the past year, I worked evenings, early mornings and weekends—pouring everything I had into this company to get it off the ground and where it needed to be. How could this happen? After everything I planned for?

Funnily (or not as funny) enough, I was in this same position two years prior on a trip with my brother when two of my team members resigned right before my first vacation.

I thought to myself, “This is a direct reflection on me as a leader, and I am failing at every organization.” I took personal responsibility for everything. "This was my fault."

So here I am, two years later, on the first day of my vacation halfway around the world, breaking down, physically unable to pick myself up from the floor.

After one (or several) Aperol Spritz, I made a promise to myself: I would finally take the time to do some deep introspection on who I was outside of “Danielle, the employee.”?

Untangling my Identify from my Career

Everything always looks so rosy on the outside, but on the inside, it was a constant battle of crushing it and being crushed (mostly the latter). Having immersed myself in early-stage tech companies since undergrad, collaborating closely with founding teams and executives, detaching my identity from my career became a daunting task.

The expectation that work should always bring fulfillment led to internal conflict. How am I supposed to untangle my identity from my career? Having the expectation that work will always be fulfilling can lead to a lot of suffering. So why was it so difficult for me to let go?

I was committed to better understanding who I was and what my needs were both professionally and personally. I tried to do that, but it was incredibly difficult while also running an?organization. After a couple of months, I decided if I was going to do the work on myself, I needed to step away from my role and my other commitments and take a real break.

After giving my two months notice, I finally had time to do that. I needed to figure out what I valued. What inspired and challenged me? What was important to me in an organization? Where did I want to focus? What did I want professionally and what did I want personally? What made me happy? And what life did I envision for myself in and out of work?

“When you don’t take an active role in determining what you value, you inherit the values of the systems around you.” ― Simone Stolzoff, The Good Enough Job: Reclaiming Life from Work

Coming from a background in startups and venture capital, I decided to create a due diligence framework that would be guided by objective measures that were important to me. As someone who often leads with their heart and emotion, I focused on the key criteria I wanted in and out of my next role—also what I wanted personally. This “Career Scorecard ” would go on to be a pillar in my decision-making process.

Building my Career Scorecard?

Building a career scorecard forced me to think objectively about the things that mattered to me as a team member in an organization. It also forced me to think about the type of organizations I was looking for. What experience did I want? Was it at a startup, scale-up, a Fortune-500 company? What were the things that bothered me in my previous roles? What did I want more of and less of? This scorecard was drafted and redrafted many times. I also shared it with my closest mentors and colleagues who gave me feedback, which I am forever grateful for.?

Things that stuck out to me came from a novel that was gifted to me called: How Will You Measure Your Life by Clayton M Christensen (thanks, George!). I used the lens of one of the theories (find more here ) combined with the scorecard to give me better insight into what motivated me and what resulted in job satisfaction versus dissatisfaction.

Even though I was steadfast on finding my next role, part of this break was dedicated to reenergizing my mind and body.

Things that I found helpful during my break:

1. Relieving all expectations of myself (surprisingly difficult)
2. Taking full days where I did whatever I wanted to not focusing on finding a job?
3. Bringing activity back into my life like skiing, going to the gym, and yoga
4. Connecting with my mentors and close community of friends?
5. Reading and getting inspiration from books that weren’t all business focused (I would highly recommend: The Good Enough Job , by Simone Stolzoff; Dune , by Frank Herbet and King: A Life , by Jonathan Eig)?
6. Finding an Executive Coach with the experience I was looking for?
7. Giving myself grace when I needed it (much tougher than I thought)

Where Am I Today?

Well, I am actually on a bullet train traveling from Tokyo to Kanazawa in Japan enjoying cherry blossom season. It's been almost 100 days of funemployment (but who is counting). The past three months have been some of the happiest days of my life. I have had the time to fully unplug and refocus on myself, my family, and my friendships. In this journey I also found a trainer, a nutritionist, and an executive coach which have all led me to becoming more attuned with my body and mind.

I am excited to share that I have accepted a job offer and am going to be starting the next chapter of my career with a role and organization that aligns with my values, motivations, and career scorecard. My grandpa has rejoiced now that he knows I won't be have to move back home to live with them, which was his first comment when I told him.

I hope my story inspires you as you think about your career and shows you that it’s more than ok to step away and take a break sometimes without knowing what’s next. I hope it also reminds you to give yourself some grace—it’s not all rainbows and butterflies. Work is hard, and I would argue it’s getting harder with constant connectivity and expectations placed on us.

I’m truly grateful to every person who has reached out, my mentors who have been there for the hard conversations, and the unwavering support. Also, I would like to thank Jamila who gave me the courage to write this and helped craft my story (this was not written by GenerativeAI, I promise).?

__

Please note, this is my experience and my experience alone. Deciding to resign is circumstantial, and I encourage you to make the best informed decision for yourself.