The 2 Insights That Led Me To My Radical Career Change


Much has been written about today’s Millennial workers who enter their professional career expecting to change jobs and even professions multiple times throughout their working years. From this perspective, more than a few years in the same role feels like stagnation, or even punishment. The opportunity to make a drastic career change doesn’t feel so daunting if you expected to do it in the first place.

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But, what if you’re not a Millennial who’s quite comfortable in an environment of rapid change? What if, like me, you looked to your professional career as a safe harbor of stability rather than a multi-chaptered book of adventure? When an opportunity to change presents itself, even the most promising chance of a great outcome can feel like a Thelma & Louise moment. How can a person with this mindset navigate the fears and uncertainties in order to embrace the adventure of change?

Five and a half years ago, I faced just such a moment. I was happily working as a criminal prosecutor — the only career I had ever wanted. I had been at it for over a decade, during which time I had achieved a level of mastery that comes from a lot of “live-fire” experience. Whether it was in the courtroom with a jury, in a conference room with a witness, or in my office with law enforcement investigators, I knew the rules of the game, the lay of the foul lines and the unique angles of the outfield wall. In short, I enjoyed the confidence of being an expert at doing my job.

On top of that, I LOVED my job. As I explained on the TEDxDayton stage, my role as a prosecutor was more than a good job or even a fulfilling mission for me (thought it was certainly that!) — it was an identity that defined me as a person. As a result, changing careers was quite literally the furthest thing from my mind as the calendar flipped to 2012.

Then, one February morning, my court-reporter friend came up to me after court with surprising news: she had a friend who wanted to talk to me about working for him at a large, private sector corporation. Opportunity had come into my comfort zone and knocked … and I laughed. Literally.

“Why?” I asked. “Do they prosecute crime? Because that’s what I do.” The thought of making a radical career change in my late 30’s seemed absurd to me. Yet, after two months and nearly a dozen meetings, a radical career change is exactly what I ended up doing.

Now, I know what you’re thinking. Believe it or not, the chance to make more money was not why I agreed to leave the comfort of my expertise behind and venture into a totally foreign world of executive business management. In fact, during the two months that I weighed the prospect of making this move, I didn’t know what the new position paid. Frankly, I never asked. I didn’t want to know. If I was going to seriously consider changing my career plan, I wanted to do so free from the distorting effect that comes with the allure of a higher income. I had already found what Jim Collins recently described during his appearance on The Learning Leader Show as my “personal hedgehog:” the intersection of that for which I was passionate about, wired for and capable of earning a living with. I loved my job, I was good at my job, and I was perfectly happy with what I was paid for doing my job. This was not something to risk merely for some extra coins in my pocket, especially to enter a new field with no guarantee that I would enjoy it or even be any good at it.

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So, if not for better pay, why did I make the decision to get off the highway of my successful and fulfilling career, and begin down the road of a brand new and unfamiliar one? It really came down to two pieces of piercingly wise insight that I got during those two months as I weighed the choice before me. That the source of these wise insights was my Wife just confirms what a lucky guy I am.

Read more leadership thoughts from Lance at his website, Leading With IDEAS, or watch his TEDxDayton talk about the problems of using labels to define instead of merely describe ourselves.

The Meaning Of Missing What You Will Be Leaving

One night, while watching a crime drama on TV as I considered the possibility of leaving my career as a prosecutor, I felt a taste of the sadness I knew I would feel if I left.

“I can’t imagine not doing this!” I said to my Wife, gesturing to the show on TV as a proxy for my real life work.

“Yeah,” she said. “You will definitely miss doing what you do now. But …” What she said next was the moment of brilliant insight: “Whether you are supposed to take this new job or not … whether this opportunity is God’s will for you or not … either way, you’re going to miss being a prosecutor because you love doing it. So, you can’t use the emotion you will feel missing it as a guide toward figuring out whether you should stay or go. You will miss it in both cases.”

I instantly knew she was right, even though the idea had not occurred to me before then. If I saw myself in the future feeling regret about leaving, that may be a sign that doing so wasn’t the best choice for me. However, it wasn’t a future regret I felt, but more like the sadness we feel when something good has ended. Far from being a red flag like regret, mourning the career I would be leaving behind was simply an artifact of my emotional connection to it.

My Wife was right: if I was looking to discern if I should take this chance, the emotions I would feel about leaving would not be a reliable method for doing so.

The Value Of Being Re-Potted

Sometime later, I found myself searching through the posted job openings at the website of my possible new employer. I was looking for any listings that included the title of the position I was being measured up for. In the absence of any prior business/corporate experience, I was searching for any insight into the responsibilities I was considering signing up to bear. When I found one and read the list of expectations — written in a pitch-perfect dialect of corporate HR-ese — I was taken aback.

“Oh my,” I exhaled to my Wife. “I don’t know what most of these even mean, let alone how to do them.” I then read off the laundry list of duties and responsibilities.

“Yeah, that’s pretty different from what you know, that’s for sure,” my Wife said. “You know, it wouldn’t be a wrong decision to stay where you are and not take this opportunity on account of how very different it is from what you currently do. You love what you do, and staying there wouldn’t suddenly become a bad thing. However …”

A slight pause.

“Even though that wouldn’t necessarily be a bad decision, it could be a bit like a potted plant saying ‘Nah. No thanks. I don’t need to be repotted. I’m good where I’m at.’ Leaving the plant in its current pot won’t kill it or do it harm. But, it could limit its potential to grow even bigger and be more productive than it can be where it is right now.”

Again, she was right.

Too often, we view decisions of whether to take a new path vs staying on our current path as a binary right/wrong choice. We think making the “right” choice leads to positive outcomes, while making the “wrong” choice leads to the opposite. Often as not, though, that simply isn’t the case. Many times, we are faced with two “right” choices … and sometimes two horrible ones. (I’m looking at you, 11/8/16.) In these situations, the challenge isn’t about making the right decision. The real challenge is understanding what you most need in the context of your circumstances at the moment.

For me, at that moment in my life, I needed to grow. My childhood experiences formed in me a deep-seated craving for stability and security. There is nothing wrong with these things. They are necessary elements of a healthy life. But, as I was approaching the mid-life point, my psychological need threatened to turn them from protective walls of safety into the restrictive bars of a self-imposed prison. If I was to grow, at some point I would have to leave my comfort zone and expand into something different. As I looked back down at the job listing on my laptop, I realized that this strange opportunity to leave what I loved was offering me a very different and much larger pot to replant myself in. In the end, this is why I took the chance and made the decision to jump into the new world of corporate business management.

The transition was a swirling experience of conflicting emotions:

• excitement at the feeling of having all of my brain’s circuitry come alive with the challenge of learning so many new things;

• mourning the end of the working relationships I had forged that would now have to transition to that category of “friends from places past,” where the bonds of connection would have to be maintained through much less frequent communication requiring much more work;

• loss of the sense of duty and mission that had been so central to my working experience;

• deep gratitude at the financial windfall that would enable me to finally put my student loans to bed for good;

• and the psychological insecurities that came from moving from my prosecutorial world of professional expertise and skill to my new experience as an absolute newb in an environment where even the newest hires straight from college knew more about working in a corporate business environment than I did. (This unsettling feeling was way more intense than I ever imagined!)

Now, over five years later, I am so glad I made the leap into the unknown. Though I missed my old career for awhile afterwards — just like my Wife had predicted — I never once felt regret and the desire to undo what had been done. I have grown immensely in the time since I made my career change. I have learned and experienced so many new things, and have developed an entire new set of skills I never would have had otherwise.

As I have shared my experience with others, it is clear to me that the value of those two nuggets of wisdom I received from my Wife were not uniquely valuable to me only, in my specific set of circumstances. Whether a strange new opportunity has come knocking on your door, or whether it is simply becoming clear that it is time to start seeking out opportunity for yourself, they are both equally applicable to you as well.

1. If you enjoy what you do, who you do it with, and where you do it, you will most certainly miss it those things whether or not leaving is what you should do.

2. Deciding to not do something radically different may not be a bad decision at all. However, there is a limit to how much you can grow by staying in the same place, doing the same thing.

One last bit of advice from personal experience: if you can afford to, take a break in between. Even a career change that is desired will necessarily involve a host of mixed emotions. Take a week and give yourself time process through them. Mourn that which you are saying goodbye behind you, so that you can, in turn, fully say hello to and embrace that which lies in front of you.


Read more leadership thoughts from Lance at his website, Leading With IDEAS, or watch his TEDxDayton talk about the problems of using labels to define instead of merely describe ourselves.