10 Lessons I Learned from Changing Careers 6 Times

decision making is listening

by Jeff Hittner

What to expect when you’re going through a career transition.

How do we come to question what we were educated to believe?  We’re brought up being told that if we study hard and work even harder things will fall into place. We’ll have the career and life that we want.

But somewhere along the path, incessantly focusing on the next financial step and the next promotion, the money-driven corporate mentality begins to eat at our soul.

The status quo careers are designed to unleash the potential of anyone except you, with work that affords you only enough to keep hanging on to it.

We don’t need to be in 3-hour conference calls. We don’t need to drive an economy we don’t believe in. Instead, we can help build the one we want to move everyone to: an economy that is circular, not depleting our resources, one that is designed to help us explore and then unleash our unique potential in the world.

The chasm between a career on our own terms and the status quo is large, dark, and scary for anyone courageous enough for the journey.  Fumbling our way across is a natural part of the process. But there are so many things I wish I knew before beginning my transition(s), spots where I could have, with a little bit of insight, struggled less, been more confident and comfortable.

After all, I’ve changed careers 6 times. 

I’ve been an eCommerce product manager. I’ve been a strategy consultant at IBM. I’ve founded several social ventures, including Ethikus, the first community of ethical consumers and small businesses in NYC that shared the same values. I’ve been a leadership professor in an MBA in Sustainability program at Bard College I helped to launch. I was even the ethics teacher to 195 eight, nine and ten-year-olds. And today I run Project X and consult to the largest non-profit on the planet dedicated to youth entrepreneurship and workforce development. Of course, finding these opportunities has been harder and messier than any description could imply. There have been gaps between roles, long moments of fear and uncertainty, whispers in my head about stability vs. fulfillment. 

Knowing what to expect before jumping into career change can help this journey be a little less intimidating and lonely. 

Here are my 10 favorite lessons from bucking the status quo:

1. Your ego is bigger than you think.

Sure you (aka me) talk a big game about blazing your own career path, but soooo many people around you are still drinking the kool-aid and that is both tempting and disconcerting. Yes, avoiding certain conversations with your consultant/lawyer/banker friends is helpful, but keeping your ego in check is bigger than this. I’ve got a laundry list of activities I fall back on when I feel the envy of certainty and simplicity of giving in to the status quo approach. I write — a lot — about what is important to me, about what brings me gratitude, about my vision for myself. This last part I do in 30-day, 90-day, and 3-year increments and it’s never focused entirely on work.

2. Who told you that you should never take a pay cut?

Living on less each month is easier than you think. The problem is not downsizing, it’s the addiction to spending. “Sure, I’ll split that $60 bottle of wine with you.” “Yes, I’ll go shopping with you.” Chances are you’ve built a life (and a habit) of spending in ways that represent your income. What I found amazing, however, was just how easy it was to live at a simpler income level once I got through that first month or two. You learn what things (and expenses) to say yes and no to. But most importantly, you discover that your happiness does not decrease with lower living expenses. Why do we accept the idea that we should always be making more money as the gospel?

Related: You Are Not Behind In Life: Rethinking Success

3. Deactivate your Instagram profile until you settle into your journey.

The truth is that my fondest memories during each career change were formed while having profound conversations that led to challenging decisions, which never would qualify to the level of “a curated Instagram moment.”  Scrolling through your feed on a nightly basis can do damage to your vulnerable transition psyche. We all know that what shows up on our Instagram feed is an idealized version of reality. It may not have been designed to be a comparison tool, but it is, so let it go.   

4. Build your community of like-minded status quo busters early in your breakaway.

I have wonderful friends. They’re empathetic, caring and amazing to spend time with. But they all have corporate jobs. Seeking out a group of folks that are blazing their own path and can form your informal “mastermind” of support is a huge benefit because they will be living the ups and downs too. A fellow entrepreneur has a 90-minute Zoom video call every two weeks with five people he’s met at conferences. They’ve all got their independent online businesses and they all support one another through their bi-weekly gatherings. 

5. Don’t measure your daily worth by the completion of your checklist.

We’re obsessed with productivity, so our workday can feel unsuccessful if we don’t accomplish. For many of us, that measure of accomplishment is a long to-do list. When we’re in transition, this list is generated by us. Yes, you’ll want to set goals for yourself each day, but find measure and have other ways to reflect on a “successful” day. For example, I set out to have one meaningful conversation each day and check in with at least one friend. If my checklist is far from complete, I rely on this to pat myself on the back. 

6. Micro-experiment the sh#$ out of your work.

Boss or no boss, it’s far too easy to get stuck in tunnel vision and planning, planning, planning. I’ve challenged myself to share my work at least once a week — if not more — for feedback. If you’re writing, send what you wrote to five friends. If you’re planning an experience, run it by your craziest friend and see if they love it. 

7. The status quo sets boundaries that you don’t even recognize until you bump into them.

I took six breaks today. SIX. Do I think I had a productive day? Hell yes. I didn’t realize the idea of being glued to my desk for eight hours straight was what I considered to be productive until I stopped doing it. But it took a while for my mind to get there. I still sometimes ask myself, “Did I spend enough time at my desk today?”

Boundaries are made up by someone else’s (read: corporations who want their workers tied to their desk ‘till death do us part’) system. Try breaking out by having mid-afternoon coffee with friends or doing your grocery shopping at 10 am.

8. Prepare for rejection and failure.

We are not experts at change or transition. We will make lots of mistakes. I’ve consistently underestimated the length of time each transition would last. I’ve compensated for this by being overly conservative on the savings I would need and by getting 100% support from my wife because, at the end of the day, I need a pick-me-up from my failure of the day.

9. If there’s something you hate about yourself, it will feel magnified during your transition.

We’re all imperfect and have habits we hate. When we’re changing careers, we are overly sensitive. That often manifests itself at being uber hard on ourselves. I take 45-minute breaks to watch episodes of the West Wing over and over. Yes, I admit it. And it makes me so mad. I think of all the better ways I could have spent that time “bettering myself.” I’m still working on acceptance…

10. Committing to a morning ritual is vital.

When you’re suddenly out of your regular 9-5 (or, let’s be more realistic, your regular 8-10), it can feel disorienting. With a calendar no longer blocked with pointless meetings and conference calls, what will you do? Whether we like it or not, the corporate structure is designed to tell us what to do, to move us along a conveyor belt of work in progress. A daily routine is valuable, too, but it’s the morning ritual that keeps you moving forward in your transition. Mine touches on everything important to me: faith, family, inspiration, action, and creativity. I meditate and say a prayer. I write down five things I’m grateful for. I set my three actionable goals I will complete that day – and usually, only one or two of them revolve around career stuff. Then I read something inspirational (and when I’m rather tired, I watch a five-minute YouTube video from a movie or show — like an MLK speech — to get my blood flowing).


So now what?

Turning your dream of fulfilling, purposeful work into reality is hard (if it weren’t, we would all be happily employed doing work we love). Yet, there are ways in which you can make this journey a little easier for yourself. Know what to expect, don’t be afraid to experiment, and surround yourself with like-minded people and we guarantee: things will start to happen for you. And in the process, tell us how it’s going!

Leave a Reply