What Outcome Matters To You?

I brain dump (pt 1 of 2) my thoughts about career satisfaction, progressions, and paths.

In this post:

• Fumbling through questions about the meaning of the word career

• Detailing some of challenging career moments of my last year

• Exploring questions that help define how to chart a career path

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What is a career?

Is it defined by an extraordinary expertise? Is it defined by longevity at one or more companies? Is it defined by progression towards the top? By leading bigger teams? Shipping bigger products? Selling bigger contracts?

I’m lately contemplating the concept as a whole. If you just wondered: does he overthink things? Yes, chronically. And I’m working to change that.

Stylized me overthinking everything.

There are numerous writers exploring portfolio careers. The portfolio career concept is straightforward. You earn income not from one source but from multiple sources. Writers like

Anna Mackenzie

and

Jules Fedele

are well down the path and graciously sharing their frameworks.

But I think there are two fundamental questions at the root of career choices:

• How do you want to spend your time?

• Who do you want to spend your time with?

A lay off forced me to confront both questions, again.

I was working in a senior multi-discipline role. Happy. Pleased with the people in my working environment. Not working too much but not monk-like calm in work mental-state. My wife was also very busy, roughly 6 months through a new job. We were straining to balance our non-work priorities with work demands.

Then, on April 1st, I received the pink slip. Laid off. Not an April Fools joke!

It was my first day back at my home desk after a vacation with my family, during which I worked on and off to accelerate a small handful of enterprise sales efforts.

It was 9 am. Monday morning. And I went from working to not working in less than 5 minutes. I remember letting out a huge sigh, my lips flapping, catalyzed by that what just happened feeling.

I didn’t immediately jump into career action.

But I kept one conversation on my calendar. I spoke with the CEO of a company that sells software that powers enterprise demos for other companies. I informed him of newly-free status and we talked about career routes that involved pre-sales, technical sales, and solution engineering, all roles germane to his software.

It lifted my mood. It gave me a few ideas. But I wasn’t ready to jump back into action.

Then, the next day, I went for a long walk. 4.5 miles. It was 1 hour and 40 minutes of thinking time. Processing time. Time to admire the sights and the sounds of the trail system across the street from my house.

Fast-forward to today. I’m a smidge over 9 months from that last role. And I’m building a consulting business that is already thriving. I’m paid well. I’m enjoying my engagements. The legal and administrative burdens are less exciting, sure, but also new and learning experiences too. I determine my day and my destiny.

Yet, I’m unsettled. I wonder if my business is the right path for long-term viability. What if I work through a successful year and my leads dry up? What if I lose my passion for it?

Have I ruined my career? I don’t know.

Another question bounces around in my brain: what are you solving for?

I think the question is better thought of like this: what outcome matters to you?

I’ve learned that I’m not willing to give up on some areas of life. I see my kids all the time. They’re 6 and a half and 3. It won’t be long before they’re independent and not quite so snuggly and attentive to me. So, this is the time to enjoy their curiosity and energy, right?

Work-from-home flexibility is important. I don’t need to be in an office all the time. But I don’t need to be at home all the time. That conclusion is a key eye-opener for me. I miss being near and around people, and working with teams, and developing intra-company relationships. As an aside, this desire is one reason why I work in New York City once per week. It helps me ingest and feel the energy of people and not sink into the stasis of my house.

I’ll cut here, for now. I have client work in front of me. But that will help motivate a follow-up on Friday.

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