“Nature loves courage.” ― Terence McKenna

“Are you struggling with your breath again?” my Dad asked as we strolled along a lakeside path in Trillium Park, glimpsing views of the Toronto city skyline.

It felt like years since I could get a full, unrestricted breath.

My anxiety had run rampant since graduating as I toiled with the question, “What am I doing with my life?”

Out of school, I landed a job with the Government of Canada.

The people were great and — as every family, friend, and stranger informed me — the pay, benefits, and work hours were unbeatable. 

But I wasn’t fulfilled.

I didn’t wake up excited to go to work or find immense meaning in the impact of my job.

I envisioned how the rest of my life would play out if I stuck around…

Work hard, please your superiors, and hope to get promoted to Manager by your late twenties. Do good at that, play the politics game, and you might have a shot at becoming a Director… who knows, maybe even Director General!

I could’ve put in my thirty years and been retired to a beach hut by age 53.

But deep down, I wanted more.

No.

I needed more.

And anxiety plaguing my breath was my body’s way of letting me know.

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Taking the Plunge

“As you start to walk on the way, the way appears.” ― Rumi

For well over a year, I suspected I might leave that job.

I thought about it daily. Journaled about it. Planned for it. Even wrote my letter of resignation months in advance.

I knew staying was a sign of complacency and a surefire path to regret.

Regret for having not tried the thing.

I was okay with trying and failing, but not with never having the courage to try at all. 

When I finally made the decision to leave and quitting was only a few months away, my mind found new concerns to occupy it…

How are you going to make money?

What if this impacts your future employability?

Is this going to set you down an irreversible life path to poverty, failure, and even greater regret than if you just stayed?

The rumination was ceaseless. 

But as soon as my final day of work passed and I shipped back my computer, something surprising happened.

My mind went calm.

Taking the plunge erased my anxiety.

I wasn’t worried. In fact, I was more excited and optimistic than ever about the future.

Once I started to walk the way, the way appeared. For me, that meant throwing myself fully into writing and travel.

I hurled myself into the abyss and discovered it was a feather bed.

Terence McKenna was right:

Nature loves courage. 

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My Advice

If you’re in a similar position with your career (or in the process of making any bold decision), here’s my experience-based advice:

• Don’t make a rash decision. There’s no rush. It’s much easier to quit than to return to a job you regret quitting. Take your time, sock away cash, and build the certainty and conviction required to make this decision and feel confident that it was the right one — regardless of how the future pans out. 

• Try to make it work but don’t fool yourself. Throw yourself completely into your work. Dive in, work hard, and see if you can find what you’re looking for. If you do that and still feel unfulfilled, unexcited, and complacent, it’s time to take bold action.

• Keep a vine in hand. If you quit without grabbing a new vine first, you might fall forty feet and faceplant. Start a project or make a plan well before your last day. You need something else to pour yourself into.

[This was a follow-up post to my popular article: I quit.]

If you’re fighting the same battle and want someone to speak with, I’m happy to chat.

You can reach me by replying to this email, leaving a comment, or sending me a message on LinkedIn or Twitter.

Thank you for reading. It means the world to me!

Much love,

Jack