Hey, OTB community! Every few months, I run a "mailbag edition" — where I answer questions from readers. You can read previous ones here and here.
Today, I'm answering two questions...
- When my jobs ends, who am I?
- What's the best pathway to success?
If you ever have questions, just hit reply or email me at hellojasonfeifer@gmail.com.
Question #1: When my job ends, who am I?
Val asks me:
"I devoted my career to one company. It just closed. I'm now grieving — not just for a job, but for my own sense of identity.
I turn 50 next year, and for the first time, I'm sitting down to really ask the hard questions: What am I good at? Who am I without this position? And yet, right now, I feel deeply lost.
Do you have any guidance as I navigate this transition?"
Val, I know you know this, but I'll say it anyway: It's OK that this is hard. You devoted a lot of your life to that work — and in doing so, it became part of you. Now you're carrying around boxes labeled "my identity" and "my purpose" and trying to find somewhere else to put them.
This is why, in time, you'll be so thankful for this transition.
When we're inside something for a long time, whether it's a company or a relationship, we often stop asking ourselves the questions you listed: What am I good at? Who am I, independent of this? Because we have nice, easy answers available! We can just define ourselves by our tasks, our roles, or our bonds.
But the trouble is: Everything external is changeable. We cannot fully control the fate of our companies or relationships. So when we export our identities to those things, we give up control over our sense of self.
What's the solution? It lives inside this sentence you wrote: "For the first time, I'm sitting down to really ask the hard questions." We should all be doing that, all the time. But we rarely do, until prompted. Now you're doing it.
You'll feel a burden to have answers. Please release yourself from that. Transitions happen in phases, which go something like this:
- Grieving
- Asking big questions
- Experimenting with answers
- A rediscovery of self
Each phase is distinct. It's helpful to recognize where you are, so that you don't carry the expectations of every phase at once.
Right now, you are at that second phase: You are asking big questions. You don't need answers in this phase. Asking the questions is the work. Confronting the unknown is the accomplishment. So give yourself the grace and time to ask, and wonder, and stare into the great open sky until it stops feeling like you're falling into it.
Answers will come. It won't be easy. But nothing good ever is.
Question #2: What's the best pathway to success?
Junaid asks me:
"I'm inspired by your career journey. Like many of us, it took you decades to reach the kind of goals you once imagined.
But I'm curious: If you were starting again in the 90s, and you didn't want it to take decades to reach the same destination, how would you do it?
Would you still choose Warren Buffett's slow, steady, and calm path, with compounding moves? Or would you lean toward Elon Musk's insane sense of urgency and accelerated execution?"
The pathway to success isn't that simple, Junaid. So before I answer your question, here's a critical learning moment from my career.
It was 2003. I was one year out of college, and I had huge ambitions to write for the world's largest newspapers. But instead, the only job I could find was at a dumpy little paper in a tiny town. So I worked there, miserable and bitter.
One day, my boss wrote me a letter that called me "a detriment and a drag on the newsroom." He gave me two weeks to turn my attitude around, or I'd be fired.
I was indignant, and I quit. Eventually, I realized my real problem: My ambitions were larger than my abilities. If I was talented enough to work for major newspapers, then I'd have gotten a bigger job — but I wasn't ready. I still had a lot to learn.
Here's what I now understand: Growth comes from balancing patience with impatience. We must have the impatience to push ourselves, always believing that there's more ahead. But we must balance that with the patience for learning and self-discovery. Without both, we'll go nowhere.
Would I have liked to be "successful" faster? Sure. But that's unrealistic.
Four reasons why:
- Success is relative. No matter how much you accomplish, you will never feel like you've "made it" anyway. That's true for me, as well as every high-achieving person I know. So as we think about the right "path" to success, we must also remember how fuzzy the destination is. Success is ours to define, at any stage of our journey.
- I didn't know where I was going. You cannot accelerate furiously toward an unknown destination. You must instead give yourself the time and space to discover it. For example, at the beginning of my career, I'd never even heard of Entrepreneur magazine. I stumbled into this role, then spent years experimenting with ways to embody and maximize it. I succeeded because I searched, not because I ran.
- I didn't have what it takes. Like I said before: I had a lot of frustrated ambitions in 2003, but I also had a lot to learn. I wasn't ready for the spotlight then, and I'm glad I didn't get it. I've seen plenty of young people reach a large stage too early, and it's ugly.
- I wanted a different balance. Success (or just the pursuit of success) requires trade-offs. For example, I've never met Elon Musk, but I know many people like him — who ceaselessly push themselves to achieve and acquire more, no matter the costs to themselves or others. And I will tell you: They are often miserable. Their personal lives are a mess. They are lonely at their core, trying to fill a bottomless hole in themselves.
That's not something I want, and it's not a cost I'm willing to pay. Yes, I devote a lot of myself to work, and I still have huge ambitions. But I'm also willing to trade less money and "success" for other things in life. We all must find the right balance for ourselves.
In short, Junaid: It is not Warren vs. Musk. It is both. And also, neither.
But mostly: It's not just a question of the path we take. It's a question of how we shape the path, and how the path shapes us.
Have a question for a future mailbag edition?
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Final notes for today...
P.S. My advice for founders and career-builders: I had a blast on Erica Wenger's Trailblazers podcast, where I shared some of my own major challenges and what I've learned from the world's smartest entrepreneurs. Listen!
P.P.S. Do you hate meetings? Me too. And I had a great conversation about how to make them better. Listen!
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That's all for this week! See you next Tuesday.
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