Shaping My Portfolio Career

The Roadmap (so far) for my Journey.

Phase 1: The Cocoon

After burning out of my corporate career at the end of 2018, I felt lost. I had been living for years with no fixed address, splitting my life between two big cities (Toronto and Vancouver) and saying yes to every opportunity that came my way to further my career. 

I felt embarrassed and ashamed that at 35 years old, I still didn’t know who I was, what I liked to do or what I was good at.

Fortunately, I had socked away some money over the years and had a cushion of savings to support me in making “some sort of life change”.

So, I chose to focus on what I could control—which was to chart a new path.

For the next nine months, all my effort went into making progress toward that and figuring out my next big move. I entered what my boss, Kevin, fondly refers to as The Cocoon—that painful incubation period after an idea is sparked but not yet manifested, a time when there are far more questions than answers.

Should I quit my job and take some time off to travel and '“find myself”?
Should I move back to Vancouver, buy a place and look for a different job?
Should I move back home with my parents and go back to school? 
Should I start a business? And therefore also have to move back home with my parents?

To help me navigate this confusion, I mapped out every intriguing path that crossed my mind. What would it look like in 3-5 years? Then, I evaluated them against my core values before eventually making my decision: 

I would 1) keep my current job for the time being but redesign it and 2) get away from city life and build a little rural island home. 

While in The Cocoon, I uncovered an old dream from childhood. I had wanted to build a cabin that I could share with family and friends. A place where we could escape the busyness and make lasting memories. It would be near water, and I’d learn how to fish and sail.

Looking back now, it’s almost freaky how much my life has evolved into what I envisioned over five years ago (except I still don’t know how to fish 🎣).

Fast-forward to earlier this year, when I found myself back in my career rut, kicking and screaming my way again toward The Cocoon.

I had forgotten how dark and lonely it felt sometimes in there.

But I made it through again, and today, I am ready to share my game plan for *finally* transitioning to a portfolio career. It has taken many months of thinking, experimenting, shaping (and crying) just to arrive at this stage.

I hope it’ll provide somewhat of a blueprint for you as you move through whatever life transitions you are going through—or, if you are inside The Cocoon, maybe it’ll remind you that you are not alone and you will make it through eventually, tougher and stronger.

Phase 2: The Dream

I have always been a big daydreamer. When I was little, I would lie on my bed and daydream for hours. As an adult, I also love to plan. I think planning is my love language.

Action is my weakness. That’s why I am here, documenting my process (I need a mechanism to hold me accountable).

Before planning anything, I typically let myself dream about what I want the thing to look and feel like. Depending on my plans, the dreaming stage can sometimes take weeks or even months. It takes time for me to build the image in my mind.

The process usually involves a lot of cycling, walking in nature, journaling, meditating, and visualizing in that oh-so-dreamy theta state.

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This is what I came up with for a high-level vision of my dream career portfolio:

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Phase 3: The Plan

Once I had the dream/vision, I asked myself what I needed to do to move one step closer in that direction.

First, I drew out my dream portfolio mix based on my dream career. This would serve as a jumping-off point for experimentation.

My (Hypothetical) Dream Portfolio Mix

Fear naturally intervened to tell me all the reasons why this was a dumb idea that would never work. 

I learned from Liz Gilbert to let Fear speak, so I did. I listed the obstacles and risks that stood in my way. Then, I came up with some steps forward that Fear and I agreed on.

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From here, I was able to draw out a loose plan until the end of the year (at which point I will decide what to do next) with some initial action steps:

My theme for the next four months is ‘Experiment, Experiment, Experiment!’ (and gather feedback and data to inform my next steps.)

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I prioritized my objectives based on which ones had the most potential to move me closer to my vision.

Priority #1 is to produce free content in my key focus area to investigate demand, find my voice and determine my positioning. I chose Substack as my platform. I plan to write once a week on Sundays and share a weekly retro and update on my progress toward goals. I will also start the PocketCOO Substack after Canadian Thanksgiving to share my favourite business optimization tools for solo and minimalist entrepreneurs.

Priority #2 is to work on my portfolio and case studies. This is a weak spot for me, so thanks to a friend’s recommendation, I enrolled in the Career Strategy Lab to provide structure, accountability and direction. The point of this work is to help me reposition myself for consulting projects and to build up my confidence.

Priority #3 is to take on a project in my current company and treat it like a consulting project. This will allow me to test my theory and add a most recent case study. This one is outside my control because I need to get CEO approval. I also don’t know what it could be yet. I’m still in the research phase.

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Next week, I will share “Phase 4: The Action” which will include: 

• My four-month plan broken down into three sprints—each sprint lasts five to six weeks.

• A progress update on my goals and a recap of the week (what went well, what I learned, failures, etc.)

• An adjusted plan for the following week.

In the meantime, What are your goals for the upcoming week?