Which Way Are You Running? Learnings From A Career Transition

Repost from my 2017 Medium blog post

Some say that quitting your job is a trend.

I recently left my job without a new opportunity lined up, and hearing that what I was doing was thought of as a “trend” felt uncomfortable. Our careers, our passions, and how we spend our time are deeply personal choices. Steve Jobs was known for starting each day by asking himself: “If today were the last day of my life, would I want to do what I am about to do today?" A career isn’t something to be built based on trends.

People told me that leaving my job was risky, irresponsible, and impulsive. I don’t agree. The real risk was waking up 5, 10, or 20 years from now in a job I hated. The real risk was my mental and emotional health, the real risk manifests if I stayed.

I believe that many of the millennial stereotypes misunderstand of what is important to us as a generation. Yes, there is a segment that acts entitled and makes demands. But for the larger portion of us, what we are really looking for is to find meaning and purpose in our work. And I get that for some people, this desire feels like privilege. And I want to acknowledge that it is, but I wish it wasn't. That doesn't mean there aren't ways to work with it no matter our situation.

I’ve seen that speaking up about looking for meaning and purpose in our work is often misinterpreted as entitlement. What many companies don’t realize is that their goals (efficiency, productivity, increased revenue) are bolstered when we feel engaged in our work. There is extensive research on this topic from big names like Gallup and HBR as well as from many smaller companies. Update: since writing this in 2017, there has been a strong positive shift in more companies recognizing this and looking for ways to support this win-win.

When we are aligned on where we are going, and what we are looking to create, work becomes a win-win.

Last year, I embarked on a personal journey that led me through the twists and turns of a career transition. I learned more about myself through this journey than any other period in my life thus far.

I learned what it feels like to follow my heart.

I became increasing comfortable with ambiguity.

I was reminded that I have 100% control over the direction of my life, and how I spend my time.

Through these experiences, I became a more confident collaborator and a more grounded human. I’d embark on this journey all over again in a heartbeat, and sometime in the future, I probably will. Update: I've done this twice more since 2017.

Below are three key learnings from my journey in trying to figure out where I was headed next.


Learning #1: Define what success means to you personally, and be open to reframing the scope of what you consider success

Gone are the days that by default, success was defined by a 20+ year tenure at a given company, making a six-figure salary.

I’ve found that defining success for ourselves isn’t just about how much money we want to make (although that can be part of it, if you wish). I think of benchmarking my personal success by the things I want to learn, the type of environments and people I want to spend my time with, and the contribution I want to make through my work. When thinking about what success means for you, consider what makes you feel joyful and alive. For some, it might be money, but consider things like learning milestones or accomplishments, values you are able to live (like having flexibility at work), or the impact you have on something that is important to you. I did a TedX talk on this topic here if you want to spend some time thinking about this for yourself.

I also urge you to consider what other permutations of success could look like that might be outside the bounds of just a full-time role. In this era full of anytime + anywhere freelance work, the gig economy, and side hustles, keeping tunnel vision on a full-time role as the primary definition of success coming out of a career transition may mean you miss what could be equal (or better!) opportunities for learning, intrigue, and/or income.

If a full-time role is your goal, engaging in learning opportunities along the way can make you a more qualified (and interesting) candidate. I would not be in the position I am today if it weren’t for seeking out things like shadowing opportunities, internships, freelance arrangements, and collaborations with friends/acquaintances on side projects. These are all ways to apply your existing knowledge while learning new skills and perspectives to progress along your journey.

Learning #2: Run toward something, not away from something

That feeling of knowing that where you are isn’t the right fit anymore, but not knowing where to focus next. It's really hard. For so many of us, the discomfort of not even knowing where to start is crippling. In my experience, being in this place of confusion is emotionally draining, and has daily repercussions in other areas of life (relationships, health, etc.).

I won’t pretend moving through this confusion is easy, but it is worth it.

I found that the most important thing for my wellbeing, my sanity, and my career was to ground my energy in looking forward even when it felt like I had no idea where to go. Sometimes, this felt impossible. And now, having come out the other side, I promise it isn’t.

What do I mean by looking forward? This is a form of taking ownership over your experience. Looking forward is not to say we should ignore how we're feeling and just think about the future, but rather we get to honor that how we're feeling is simply information for us. Our emotions are data pointing us toward what is really important to us that we might not yet have or feel yet.

A key step in looking forward is to identify your priorities, interests, and passions to use as the foundation to create your image of what's next. This is what unlocks the ability to running toward something new, rather than away from something that is bringing you frustration or pain.

Learning #3: Don’t let people tell you that a gap on your resume will make you look bad

If you decide to move on from your current role before you know what you’ll be doing next, the knee-jerk reaction that many of us hear is often ‘but what about the gap on your resume!’

If you follow the above (Learning #2) reframing and decide to move on in an effort to run toward something new (even if you don’t yet know what that is), you have your slam-dunk explanation right in front of you.

In my personal journey, I found there to be immense respect for the fact that I moved on from a job that I identified was no longer the right fit. In order to find what was the right fit in my work, I felt that I needed time to dedicate to that exploration, and at the time I didn’t feel I could do this in the way that I wanted to while working full-time. I recognized that my staying in a role that was no longer the right fit for me wasn’t fair to myself, or to the company. (I acknowledge that this isn’t always possible for others, and that I was fortunate that my circumstances allowed me to do this.)

I’ve found that being in touch with yourself and your own priorities and values is a highly respected quality by employers and collaborators, and the amount of character this displays can strongly work in your favor. And, if it doesn’t resonate with a given person or company, that probably isn’t a place you want to work.

We all know the adage about life being about the journey and not the destination. I started my personal journey wishing I knew where I was headed, resonating with the words of The Smashing Pumpkins: “If I knew where I was going, I would already be there.” I just wished it were simpler. I wished I knew.

Looking back, I would not be the person I am today without the ambiguity of my journey. If I had known where I was going, I would never have experienced the immeasurable growth that came from having to individually shape each step along my path as I was taking it, like I was driving in dense fog.

I’d encourage you to use the process of identifying where you might be headed as building blocks in your life journey, knowing that there will be learnings that come from each step if you're open to receiving them.

You got this!