Hippie CEO Life #21 - The Road Not Taken

September 2, 2022

“Two roads diverged in a wood and I - I took the one less traveled by, and that has made all the difference.” ~Robert Frost

One of my favorite lines, from my one my favorite poets. i think about this line often as it applies to my professional journey.

Coming out of college, i believed that my path was to be the well traveled one. Graduate. Get a good job. Be a solid corporate citizen. Don't be a wallflower, but don't be a rebel. Get promoted into management. Work really long hours to impress (kiss up to) the “right” people. Become an executive with a fancy corner office. Get all the monies. Then finally, start living the kind of life that i want to live.

And indeed, i did go down that path a way. Getting a job out of college at a decently sized, publicly traded company. 6 years playing the corporate game until i got fired, walked out of the building, told to never come back.

i hated the well-worn path, so i turned around. i worked for a few more companies on the path, as i journeyed back to where those famous two roads diverged in the woods. With each step, becoming more and more convinced that i was meant to be on the one other road, the one less traveled by. Perhaps there i could work, i could learn, i could advance my knowledge, and mostly importantly, i could do all those things by being me, not by being someone others wanted me to be.

i reached that pivotal point in the woods, the year was 2013, and without looking back, i grabbed my beat up Patagonia pack and started off down the less traveled road.

As i traveled and pondered my previous journey, it wasn't so simple to call it this road or that road. Even on that well-traveled one, there were many side roads, many decisions to be made, that often resulted in choosing the less traveled one. Taking a job for considerably less pay in exchange for much more responsibility and exposure to more complex problems to solve. Rejecting a very high paying job, at a very influential tech company, because the required travel schedule didn't align with my idea of a happy life. Choosing to directly reject orders from my management team to fall in line, become a good corporate clone, because i was done being a puppet.

Our careers are incredibly complex. There is no "one size fits all" path that is guaranteed to lead to professional success. And while my path now is the less traveled path, that doesn't mean it's the "right" path, it was just the path for me. The path that makes me happy. For others, their right path may be the well traveled, corporate path. For others, it could be a path that is so hidden or out of the way, we can't even see it.

i guess the point of all this rambling is that it is so important to be open to exploring and going down different paths, sometimes back tracking and starting over again, until you find the path that speaks to your soul, that fills you with energy to create, that makes YOU happy. Not the path that you think others want you to be on, but your own unique, special path, that gives your life meaning.

The Road Not Taken
by Robert Frost

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

Thank you Jess for suggesting the topic for today's newsletter and thank you all for being a valued reader. While i started this newsletter as an outlet to just write my random thoughts, a way to get them out of my head, the fact that people are getting value and inspiration from what i write just means the world to me (A special shoutout to my father-in-law and brother-in-law who have been great supporters of both my writing and views on how work should be done).

If you are enjoying my writings, please share this newsletter with a friend or colleague. And finally, if you have a topic suggestion for a future newsletter, please send me a note @usujason.

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