How to Reach Career-Actualization (In 12 Months)
The step-by-step guide to reaching the highest version of you

I’ve had my fair share of career meltdowns.
I remember crying into the living room carpet thinking my life was over (at 23, lol). In hindsight, a ‘career’ is a right mind flipper.
Here’s my short but sweet 9-year career stint:
- At 21 I thought everything was going right
- At 23 I realized everything was going wrong
- At 24 I’d never felt worse about where I was
- At 29 I am straddling various careers (and feeling good about work)
Today I’m able to breathe a little (after a long renovation) and I’m starting to think about what I want my life to look like. A question I keep coming back to and a concept I’ve just made up is called career-actualization.
That defines a career that is:
- Financially fulfilling — makes you enough money to live the life you want now (and later).
- Creates the highest version of you — pushes you enough to grow, not too much to overwhelm you, and allows you to operate at your highest version.
- Lifestyle design — allows you to live the life you desire, including where, when, or how you work.
- Joy — At least 70% of your day is full of the stuff you actually like to do, allowing you to work in a flow state.
You see, careers look different for everybody. I personally wanna walk my dogs, enjoy the countryside, not manage people and spend time doing work I find fulfilling. To some, that’s their idea of hell.
That’s why I’ve defined career actualization above. So let’s get into how you find career-actualization…
1. Your foundation is self-awareness
“Knowing yourself is the beginning of all wisdom.” — Aristotle
There is little hope for career-actualization without self-actualization. You’ll likely never find happiness in work if you don’t know what fundamentally fuels you.
Or better said: who you really are.
Now, an essay on how to figure out who you are would likely last a lifetime. But there are a few things I’ve found useful as thought experiments to help me go from unbelievably confused to self-aware-ish.
Here they are:
- Don’t make any decisions, especially life decisions, when you’re in a heightened state (hungry, emotional, bad day, frustrated). Snickers were right, you’re really not you when you’re hungry.
- Self-awareness is a journey, getting to know yourself is a process, and you never stop — More you explore, and even when you have explored one space, you go back years later and find something you didn’t see before.
- Aim for directionally correct, you’ll never be 100% with 100% of the information, that simply doesn’t exist. Instead, aim for mostly right with the information you’ve got.
One of the best pieces of advice (I think I gave myself, not 100% sure) is that you’ve got to accept that you don’t always know all the answers, and that’s part of the fun.
Life isn’t linear.
2. Failure is more profitable than success
Nobody talks about failure.
The truth is that failure is the path to success. Failure is the most fruitful of all endeavors, the trouble is it gets overshadowed by shame.
Whilst you feel bad for your failures, you miss the beauty of them, all the lessons that are to be learned right in front of your eyes. Failure is the biggest missed opportunity that exists.
If you want to reach career-actualization, fail. Fail hard. Fail shamelessly. Fail unapologetically.
Failure, deep failure, failure that you feel in your bones, that you assess under a microscope, failure that you are tuned into, that’s the sort of failure that will propel you.
3. The fastest way to reach happiness is to measure the love in your life
Whenever you talk about careers, you can guarantee a big elephant is sitting in the middle of the room that nobody talks about.
That’s love.
“In family life, love is the oil that eases friction, the cement that binds closer together, and the music that brings harmony.” — Friedrich Nietzsche
A career compliments life. It’s an enabler. It’s a source of happiness and a secondary source of happiness.
A career exists inside life, not the other way around. Maybe you’ve got a little one on the way, maybe you’re renovating, maybe you're changing careers, maybe illness has flooded your consciousness.
A big life is determined and defined by you. And only you.
Part of achieving career-actualization is realising the role it has in your life.
4. Chase feelings, not titles
Most people do the opposite.
Why?
Because the status quo is a hard master to disobey. Instead, listen to how the work makes you feel, not what your LinkedIn profile could say.
You’ll find more happiness if you do.
5. Find your questions
If you find yourself unsatisfied with your answers, ask better questions.
Go for a walk and riff off questions.
Keep asking until you land on a question that leads you to better thoughts. Get in the habit of asking better questions and you’ll find better answers.
6. The ‘WWLLL’ Test
Assumptions cannibalize expectations.
One way to ‘try before you buy’ is to ask yourself what will life look like AKA the ‘WWLLL Test’.
How?
Find somebody doing the thing you want to do and live a day in their life.
Then ask yourself — did you want that or did you just think you did?
7. Carrey’s Distortion
This idea shook my brain.
“I hope everybody could get rich and famous and will have everything they’ve ever dreamed of, so they know it’s not the answer.” — Jim Carrey
Most people spend most of their lives yearning for a dream they seldom realize. The ‘lucky’ few achieve their dreams and are hit by the harsh reality — the success didn’t fill the gap.
Career-actualization is a state, not a solution. The realization that if you achieve everything on your list, you’ll still have problems, is sobering.
You’ll come to a new realization which reminds me of the line by Soren Kierkegaard:
“Life is not a problem to be solved but a reality to be experienced.”
It’s a piece of the puzzle, but other pieces need to exist to make the picture seen.
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