The very easy, not-painful-at-all, 5 super simple steps to changing your career

The definitely-no-pain-whatsoever guide to doing something different [Don’t Work: Part 09]

Series: Don’t Work | Part: 9 of 10 | Reading Time: 6 mins
If you’ve enjoyed The Way of Work, you can support the project by commenting, hitting the ❤️ or 🔄 below and/or sharing it with a friend.

---

This is part of the series, Don’t Work, exploring our identity and meaning around work.

---

🛑 Warning: this one is going to be a little different. I wanted to capture the feeling behind the change in direction in my career. Not just the logistics, but the emotions of it all. If you want something more tactical, then I suggest you skip this one. But, you probably didn’t come here for generic career advice, now did you?

---

Step 1: Dismantle self

Most of us prefer incremental change. The small edit to our diet. The pill that masks a problem. The listicle that dumbs down an extraordinarily nuanced transformation.

These slight changes, while fine, can pacify our resolve to make the big changes that are really necessary.

Because real change requires destruction.

Destruction of an old way. An old process and philosophy. An old identity.

Sometimes it's the destruction of old habits. The ways of doing things that got us here.

Sometimes it's the destruction of old relationships. Ones that were important to us before.

We’ll put in all this work to build ourselves up into something, only to dismantle it later. Sure, putting together IKEA furniture is frustrating, but have you ever tried taking it apart?

We talk of awakenings and new beginnings as positive events. When in reality, you awaken away from an old way of thinking. That means the foundational lens of your world is disrupted. A major part of your old life, now gone.

We think these farewells come easily. “Goodbye! Thanks for everything!” That we can move on without the pain and feeling of loss.

---

Step 2: Resist an overwhelming urge to turn back

In moments of change, our emotions are fragile. We sit on new, unsettled ground, without certainty, and filled with doubt.

While here, stuck in the middle, we contend on both sides with a leftover past and an uncertain future.

We start imagining how easy it would be to go back to the old thing. What may surprise people is we wanted the old way to work out. It’s a place of comfort. We want it to still work for us.

What? You think we’re rebelling for the fun of it?

Heck, if we could have just tweaked a few things and skipped this whole identity crisis, we would’ve gladly signed up.

How easy it would be to fall back into those old grooves. The old assurances. Every nostalgic thought beckons us back, pulling us like gravity, to the security of our old life.

But it’s this damn desire or longing or whatever it is that pulls us somewhere else. You see, we’re not in control here, and feel compelled to make a leap.

---

Step 3: Say farewell to your friends

The relationships are the hardest part. Both with others and within.

With others, we’ll get their thoughts on our change. Most of it isn’t shared out loud. But their thoughts are heard. They’re felt.

It’s usually about what was NOT said. The response comes in the form of a subtle eyebrow raise, quieter than the distant thud of a door closing. Or a long, skeptical gaze that stretches out like an awkward pause you can’t fill. But the loudest response is the absence of any enthusiasm—a deafening silence that hangs in the air, thick and heavy.

Sorry, they rarely say “good for you!” Or “I’m proud of you!”

Instead, it’s: “that sounds risky.”

Risky? You mean, like blowing up our identity? Doing something new with low odds of success? That type of risky?

Yeah, we goddamn well know it’s risky!

Part of the issue is we, ourselves, are still uncertain with the change. I mean, how can I tell you, when I don’t understand it myself?

We’ll meet our old friends and colleagues, where we’ll be asked that awful question: “what are you doing next?” And every time, we go back there, back to the dread.

In the early days of change, we leave most conversations with little reassurance. Only more questions. More doubt.

The ones who guide you, on the other hand, shine like a lighthouse amongst the fog. Sometimes, only the smallest slice of light is required. A split second of confidence that makes up for a dozen days of doubt.

And the people who give us space are as good as the guides. Thank you for these people! Maybe they have their doubts too. But they realized we are holding onto enough of it ourselves.

---

Step 4: Wage the war on yourself

But the feedback from others pales in comparison to the feedback within.

We are our own greatest judge. And we must live with that sonofabitch.

If only it were as easy as a pros-cons list!

Instead, it’s an imaginary battle royale in our heads. The strong forces of “old me”, facing off against the tiny, insignificant “new me,” armed with nothing but a flicker of hope. In our imagination, the battle does not end well.

We imagine our mentors, friends and family pressing and picking away at our resolve to change. That one person who just won’t stop asking “so, what’s next?” And we think, please, can I just not go there for like five minutes?!

We lose hope. We’re slipping.

And we’re worried that we will slide back down that hill and never come back and we’ll be stuck where we are and we’ll never be brave enough to climb the change and I just don’t have the support and I’m wasting my life and I’m never going to do anything about it and I just CAN’T!!!

---

Step 5: Turn the tide

Until, at some point, the war starts to shift.

That little, insignificant “new me” starts to win a few battles. Not many, just one or two. They’re small, almost too small to notice. But they matter. Like a seedling breaking through the soil.

We feel our self concept shifting. No, it’s not what we originally thought - it’s not a leap from one place to another. Instead, it’s a long, grueling march.

We keep marching, at first with force and fight and pain, but now a bit more naturally. The steps get easier. The destination, still months (maybe even years) away, is closer now.

The old voices slowly quiet down and disappear. Or at least, they become less significant, their words holding less weight.

The tides are turning. The new way is gaining momentum. The wins are slight, barely noticeable, but they’re there!

And that little hope emboldens us to keep pushing.

We give ourselves space to explore. Room to breathe. A playground to just figure things out on our own, without all the judgment and evaluation and shoulds and oughts.

That new thing comes into form, maybe still blurry, but it’s there. It has substance. I can see it!

Then, one day, we slay an old monster. We let go of an old way. An old relationship. Sometimes with another, but usually with ourselves.

After so much loss, we relish this feeling we haven't felt in what feels like forever: triumph.

We regain the resolve that slipped away. What was once a belief in an idea to do something new, now becomes a belief in ourselves to be someone new.

The skeptics are still out there, for sure, but they matter less now. And critically, they are not in here, where it really matters, where the final judgment is made.

And, maybe most importantly, one day we come to sympathize with the skeptics. Outside and inside. We say, I understand.

Perhaps, we might even be able to say, I forgive you. Ultimately, letting go of the old stories, old ways, and old identities pressuring us back toward a past that is no longer relevant.

And we’ll be a bit more ready, for the next time, when it’s time to change again.

Next up… well next up I’m deciding between a few different pieces for the coveted last slot in series. We’ll see what I come out with next week.

---

This is part of the series, Don’t Work, exploring our identity and meaning around work:

Part 1: Work identity serves, then severs

Part 2: Unraveling the layers of working identity

Part 3: The Value of Disappearing

Part 4: How to be unproductive

Part 5: Beyond our basic ambition

Part 6: The “Hard Work” Delusion

Part 7: Diversified Portfolio of Identities

Part 8: Scale down, after scaling up

You can support this writing by commenting, hitting the ❤️ or 🔄 below and/or sharing it with a friend. It helps others find my work.