The No. 1 step you MUST take before launching your portfolio career.

Avalyn Lim

Unlike other career moves, a portfolio career shift – especially a drastic one where you leave your corporate job altogether and launch into new, unrelated areas of work  – takes a lot of introspection.

If you’ve made the leap, you know what this feels like.

If you haven’t, perhaps it’s something you haven’t even thought about.

How we define ourselves

Like it or not, our identities are tied up a lot in our professional lives. At a party, someone will ask you what you do as a means of introduction. If a friend or acquaintance bumped into you and asked what you were up to, I’d bet 80% of the time you’d answer in terms of your industry, or role, or company, or something related to your job.

Moving out of our professional careers, or even taking a small step out of it to test the waters, can be destabilising. How do you define “what you do?” when you’re figuring it out as you go?  

Why your WHY is more important than what you’ll be doing

Chances are, a large number of us began thinking about starting a portfolio career because of one or more of these three reasons:

1.     You were bored…

2.     You were frustrated and/or disillusioned…

3.     Your job left you and you figured, “if not now, then when?”

Now, these are all great reasons to launch a portfolio career. I experienced all three (sometimes all three at once) in my weird career path. But those reasons alone will not be enough to sustain one.

Let me break down the six phases of an unsustainable portfolio career this way:

1.     Escape phase: “I hate this place/job/culture. I need to do my own thing!”

2.     Honeymoon phase: “I feel so free! The world is my oyster!”

3.     Curiosity phase: “Let me do this, and that; and maybe also a bit of something else”, coffees with friends, acquaintances, ex-colleagues, networking, networking, networking…

4.     Reality phase: “Oh crap, I don’t know what I’m doing and my friends are beginning to stress me out with their questions!”

5.     Desperation phase: “What was I thinking?” “Will any company hire me now?!”

6.     “Back to the matrix” phase: “I’m applying for this job NOW” i.e. you go back to corporate.

Now, please don’t get me wrong – there is no judgment here if you do go back to corporate. Portfolio career life is not for everyone. Heck, I considered going back to corporate plenty of times myself!

But what kept me out of the “matrix” (side note: it just occurred to me that perhaps there is another reason why many companies are matrix organisations!) was my deep-seated desire for freedom.

  • Freedom from company cultures that didn’t align with my values and beliefs
  • Freedom from work that didn’t give me joy or “flow”
  • Freedom to travel and choose my work
  • Freedom to design my lifestyle and how my family life would look like.

It was this “north star” that kept me going through the years where I didn’t exactly have a portfolio career yet, but was moving between industries and roles in search of meaning and my place.

It kept me going through the tough early years of my portfolio career, where it was more of a “trial-and-error” career.

It sustained my belief in the face of questioning looks, sarcastic jokes, snide remarks of those who thought I was nuts AND the concern of well-meaning friends.

It keeps me going even today. Because even though I run a fun, fulfilling and flexible portfolio career right now, the conditioning of my past does occasionally poke me in my sides and make me question my choices - much less often than before, thankfully!

So what do you need to do?

Simon Sinek’s Start With Why principle hits it on the head. You need to start with the Why, then move on to the How and What.

And the Why needs to be deep, values-based… purpose-driven. Not a perfunctory “because I have always wanted to do my own thing” or “because I hate my boss”.

So exploring and defining the reasons why you made or want to make this move are critically important steps. What you do in your portfolio career, and how you do it will flow from the Why. The lack of thoughtful and deliberate thinking about why you want a portfolio career will stop you in your tracks when push comes to shove.

How to get to your Why

Here are some basic guiding questions to get you started – explore your “why” by asking yourself these questions:

1.     What are the triggers that got you started thinking about a portfolio career in the first place? A push reason is very different from a pull. Are you running away from something (like I was, from the legal profession), or toward something (e.g. an artistic career that you’ve always wanted)? Are these good enough reasons to make the move?

2.     Why is now a good time?

3.     What do you hope to achieve professionally through a portfolio career?

4.     What do you hope to achieve personally through a portfolio career?

5.     What are your absolute musts and non-negotiables in life? Does a portfolio career promote or hinder these?

6.     What support do you have to keep you afloat in tough times? Someone or something to remind you of all the stuff you said in answer to questions 1-5. And who can keep you both honest (to yourself, mainly) and motivated.  

Now, I have coached enough people to know that it’s not good enough just to answer these in your head.

Write the answers down and review them over and over, so you get absolutely clear in your head AND your heart why a portfolio career is both what you want and a commitment you can keep to.

Through this process, you will get so much more clarity on the reasons you are making this move, and enjoy the highs while managing the lows.

Or you might decide that a portfolio career is not right for you – perhaps not right now; perhaps ever!

Regardless of your conclusion, the clarity you’ll get from this process is priceless.

So I wish you all the best in your exploration. You can do this!    

This post was originally published on Avalyn’s blog: