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"Throwing Away My Career" Was The Best Move I Ever Made. Seriously, though.


Daniel LeMoine is a social entrepreneur, change-maker, and writer. Here he writes at the intersection of faith, work, & building a matterful career.

"Throwing Away My Career" Was The Best Move I Ever Made. Seriously, though.

Dan LeMoine

I received this text the other day from someone close to me:   

Do you ever regret not sticking to the business path since you and Danae went to the Dominican Republic?

It’s a solid question. Here’s my response.

The short of it—Not at all. I mean, I never really left the biz path in my mind. I built a full business accelerator and coworking space, began building my body of meaningful work, and have had more business opportunity come my way in the last few years than I could’ve ever imagined if I were still on the "traditional," “safe" path.
[That’s not to say a more 'traditional' path is a bad one, I just think coming to Doulos helped me connect some dots between seeing how business can be an incredible force for good. How it can be a force in shaping culture just like we’re doing with education].

While initially, my role at Doulos was not necessarily the most logical next step in “what” I wanted to become, it was hands-down the best next step in “who” I wanted to become. And I believe God blessed that and brought the “what” in line in due time.

Serving here has been so hard in so many ways and has shaped and matured and equipped me to crush it when I re-enter the biz world full time…my business philosophy has been deeply impacted by my time serving others and trying to solve a meaningful problem in this country and give generously of my blessings to help others.

(Yea, I know it was a novel in text message terms, but they set me up for it with such a loaded question!)

When we first made the decision to buck the conventional path and move our lives to the West Indies, naturally some of our well-intentioned friends and family showed a bit more concern than they showed or shared in our excitement.

Aren’t you worried about you career path? 
How are you going to ever explain the gap in your resume?
How are you going to make money and save and buy a house!?
Couldn't you serve in your own country in your free time? #Merica!
You’re leaving a budding career to go work at a school in the third world? That’s career suicide...

Hmm...These questions aren’t bad, necessarily. But the massive problem here is that, though well-intentioned, they are rooted in fear. 

I get it, I really do. Our default mode as humans, it seems, is to be driven by fear in many areas of our lives. People get scared that someone they care for may make an irrevocable mistake or wind up in the poorhouse. They play out the worse possible outcomes and then try to steer others away from making decisions that would lead to their nightmare scenario.

But if they're honest, the fear is often more self-centered too. They get scared that if someone else in their tribe chooses an uncommon path, chooses a more meaningful story, or simply chooses adventure and life over boredom and mediocrity, that they'll be forced to question their own lives, careers, and status quo. And that’s uncomfortable and frightening. And so the response is to critically question out of fear, or worse—scoff and snicker and play the devils advocate.
[Note: I used the third person “they,” but I really mean “we” because I’m just as guilty of this fear-questioning as the next chap]

Yet, we were not given spirits of fear (cf: 2 Timothy 1:7), or mindsets of scarcity

For all of the most important things, the timing always sucks. Waiting for a good time to quit your job? The stars will never align and the traffic lights of life will never all be green at the same time. The universe doesn’t conspire against you, but it doesn’t go out of its way to line up the pins either. Conditions are never perfect. “Someday” is a disease that will take your dreams to the grave with you. Pro and con lists are just as bad. If it’s important to you and you want to do it “eventually,” just do it and correct course along the way.
— Tim Ferriss, The Four Hour Work Week

 We are called to encourage one another (cf: 1 Thessalonians 5:11)…In other words, we’re called to leave each other full of courage, not fear. 

I’m sure you’re thinking: 

Alright, bro. But, what’s the alternative? to say nothing? never ask questions (of ourselves or others)? That doesn’t seem prudent.

Below you’ll find several guiding questions you can ask (yourself or others) in lieu of the fear-based questions.

And remember: give the benefit of the doubt to the person looking to lead-up and take a big leap—it’s likely they have already confronted and battled many of these fear-based questions, naturally. They don’t need others pointing out all the reasons not to follow a call, try to make more impact, or simply do something epic, their own Fear and Resistance does that for them already.

The Alternative: 2 Extremely Powerful Identity-Based Guiding Questions

It’s likely that if you’re reading this you are a high-achiever looking to make an impact with your career, to do something uncommon or audacious in your life, searching out the uncomfortable path of growth and learning, giving more than you're taking, and trying your darndest to avoid the safe path (not because it’s safe, but because the alternative is a more meaningful one).

As you ignore the fear-based questions, here’s a few better ones to ask yourself (or others) who are about to “lead up" into a better story:

  1. "When you and I are 80 years old, looking back at your life, will you regret NOT doing this? Will you regret not pushing into the discomfort and fear that comes with finding the truest, most matterful story to write yourself into?"
  2. “Will doing this align with who I want to be individuals (or as a couple)? Will this help shape me/us into the man and woman we want to become (and the marriage God is calling us to)?

Surely, taking the uncommon path might not work. But are you willing to go anyway? knowing the transformation it WILL bring to yourself and others you connect with on the uncommon path is the true reward.

A guy I look up to online confronted the same skeptical fear-based questions before he left his budding career at a NYC startup to live in Brazil. I’m sure if we asked him, he’d tell you he returned after his time of epic-ness with more focus, conviction, and energy to crush it than he would’ve had otherwise. Here’s his take on the result of choosing the uncommon path:

"When you truly understand your life’s work and your actions are in harmony with this, I sense you’ll not only reach the greatest level of happiness, but also highest levels of impact due to the zeal and consistency that you bring to your actions.” — Scott Britton

[Want more on how to avoid making horrible decisions (or indecisions)? READ NEXT: The 4 S’s of Bulletproof Decision Making]

Trading Up

Looking back, I can say with 100% confidence, zero regret, and without question — I didn’t come close to throwing away my career as predicted by some.

It didn’t even stunt my career growth. The opposite occurred, actually. In pushing into this calling, choosing obedience over comfort, God blessed me/us with more opportunity, a more true sense of who I am in light of Jesus in my work, and a grander vision of where he wants me to go.

When I take the time to reflect on the last 4+ years of living an uncommon path, my only response is gratitude. In every area of life I’m more consistent with the man I want to become, the marriage I want to have, the career I want to build, the impact I want to make. In every area the metrics are moving in the right direction.

I’m the best version of Dan LeMoine because of where I work (and who I work with). And I don’t know many people who can say that.

There is zero doubt that I traded up and am now on a completely different trajectory than I otherwise would’ve been had let the fear-questioning keep me on more conventional paths.

End with this quote from CS Lewis’ The Lion, The Witch, and The Wardrobe. It’s a part of the story where Susan is about to meet Aslan and is sharing her nervousness with Mr. Beaver:

“Aslan is a lion- the Lion, the great Lion."
"Ooh" said Susan. "I'd thought he was a man. Is he-quite safe? I shall feel rather nervous about meeting a lion"...
"Safe?" said Mr Beaver ..."Who said anything about safe? 'Course he isn't safe. But he's good. He's the King, I tell you.”

Leading up, choosing a better story, playing at the highest level you can, is rarely ever safe. It is never conventional, and it is never easy. But it’s good.

Happy Hunting,


P.S. By the way, if you ever want to talk about this stuff or simply need a motivating kick in the ass to take the leap - call me and I’d be happy talk it out.