MATT DOAN

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Where do you go when you reach the top?

“I keep getting job offers, but they’re not appealing.”

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“I’m already at the top firm in my industry.”

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“I’m not gonna take a step down, so where do I go from here?”

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(Privileged statements, for sure. But well earned.)

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I hear this sentiment a lot from former colleagues and those in my coaching practice.

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They’ve ascended the ladder with striking efficiency:

  • Impressive logos on their LinkedIn profile
  • Promotions every two years
  • Well-padded bank account
  • 10+ years of “experience”

They’ve nearly reached the ladder's top rung — there’s just a little room left. Despite the gains, this can actually be a terrifying position to be in.

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Here, new questions creep in:

  1. Do I really want that top spot?
  2. Do I want the life of those above me?
  3. What am I sacrificing by blindly moving up?
  4. How do I stay excited and keep growing?
  5. What else is out there?

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If you’re in this spot (and kudos to you), it’s a serious predicament.

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Your “choice” comes down to three options:

  • Up
  • Out
  • Solo

Analyzing the options

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1. Up

  • Meaning: Grind upwards within your company — reach the upper echelon.
  • Pros: You unlock top-tier compensation and perks within the firm and establish notoriety.
  • Cons: After 10+ years in a company, the external world sees you as a one-trick pony. Your personal growth stagnates. You’ll eventually be forced out…and scared about what’s next.

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2. Out

  • Meaning: Leave current company and move to a new one.
  • Pros: You (kinda) shock yourself out of conformity. You gain a slight title/pay bump by “hopping.”
  • Cons: You’re still doing the same type of work. If it sucked before, it’ll still suck.

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3. Solo

  • Meaning: Self-reliantly pursue a business of your own. (Realize: it CAN involve others and does NOT require you to leave your 9-5.)
  • Pros: Entrepreneurship pushes you to develop new (timeless) skills. Opens new/unbounded income streams, relationships, opportunities. Brings excitement and (possibly) deep meaning.
  • Cons: Difficult to get the flywheel moving. You don’t have the corporate safety net. It takes real skin in the game.

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Final verdict

In almost every case, you should take option 3 seriously.

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You’re probably most resistant to this one, and for good reason: you’ve never contemplated it because (a) it’s completely foreign and (b) you’re addicted to your comfort zone.

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But just use your logical brain for a second. The “Up” and “Out” options are constrained — you have to play by their rules and you’re constrained by their caps (e.g., earning potential, type of work).

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Options 1 and 2 (alone) don’t lead to wealth (money, time, and choice to live the life you want).

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The “Solo” option, while scary, is unbounded. Your freedom, growth, and results are uncapped. It also provides you benefits that are simply unavailable within options 1 and 2.

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As in most cases in life, the least popular (non-majority) option presents the biggest possible payoff.

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Yes, you’ve got to weigh the tradeoffs. I advise you start by anticipating future regrets of action/inaction.

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In my definition, Solo doesn’t mean “alone”; it means “self-directed.”

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Solo only requires a few bucks, paired with dedicated pockets of time and energy. Low risk, immense reward.

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So, what’ll it be for you? Up, Out, Solo?

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Let me know if I can help you.

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