Six Surefire Ways to Know If a Portfolio Career Is Right for You

Avalyn Lim

When I started this blog, I received lots of questions about what a portfolio career actually is.

As I define it, a portfolio career is a professional and lifestyle choice where you integrate the activities that motivate you, give you the most job satisfaction and bring you joy and fashion it into a career of multiple mini-ventures.

It’s called a portfolio, because just like an investment portfolio, it comprises several different components that meet different needs or objectives. Unlike conventional careers, you hold multiple roles at the same time and it’s often called “going plural” or a “slash career” (as in Coach/Board Advisor/Writer).

The forms it can take on are entirely self-defined: it could be anything from a side-gig tagged on to your regular day job to a full-blown portfolio that consists of several unrelated activities. Whatever the shape or form, you call the shots, and that’s the draw!

Like any job role, a portfolio career isn’t for everyone. While the lure of a fun, fulfilling, flexible career (my 3Fs!) is indeed highly attractive, the reality is that it takes a certain amount of soul searching and self-reflection that we don’t always allow ourselves time for in the corporate world; as well as self-motivation, grit and tenacity to keep moving forward. It’s like being a startup founder, where the only person in the organisation is you.

But boo-hoos aside, the rewards are incredible. If done right, a portfolio career offers you the 3Fs and really the opportunity to craft your lifestyle in a way you may not have imagined was possible. Other “plurals” I know work six months of the year and travel the world for the other six months.

It also allows you to combine your professional skills and personal passions (for want of a better word) in a way that you can’t in the corporate world. A friend of mine combines her passion for healing others through physical therapy with her strong analytical background. Yet another blends his strategic management skills with the arts.

So how do you know if a portfolio career is something right for you and that you’ll absolutely love it? Here are six ways to find out for sure:

1. You’ve hit a career midlife crisis

Have you ever felt like even though you’ve achieved huge success already, your corporate career just isn’t enough anymore?

Whether it’s the drone of “sameness” as you go about your work, or the politics that get in the way of actually achieving anything worthwhile, you know in your gut that this isn’t what you want to spend the rest of your life doing.

There is a part of you that is absolutely sure that your skills could be put to good use somewhere else, but you ALSO know that the usual career change into another industry or job just doesn’t give you that positive buzz anymore.

It’s a clear case of “what got you here, won’t get you there” to quote Executive Coach Marshall Goldsmith. So you are on the lookout for something that can make you feel more alive.

2. Titles don’t matter - you’re interested in the freedom to make change happen

You have strong values and views that you care about. What matters to you is that your actions can tangibly make someone’s life or business better.

Now the word “impact” is bandied about everywhere and I cringe as I write it, but that’s really what a thriving portfolio career is built on.

Caring for a certain cause, business, or community of people, making a difference, and being able to see the impact of your actions can make is what you’re after. And the cherry on top: you want the freedom and independence to make shifts along the way so you can be even more effective!

3. You crave variety

A portfolio career is a little like Executive ADHD.

What I mean by this is you’re someone who has interests in a variety of things, and you can’t sit still and just do one thing for long. If you catch yourself thinking “what else could I be doing now?” - in the middle of a meeting or 6 months into your job - a portfolio career might be the right type of role for you.

A word of warning though: this variety of the portfolio career suits our variety-loving personality but it also exacerbates it. So if you are going into the gig economy with a portfolio career, self-discipline and structure are super duper important!

4. You’re a fast learner

If it takes you half the time to get up to speed on most things than it does others, you know that it doesn’t take that much to adapt to new fields.

Because you have the ability to pick things up quickly, your strategic / management / operations / marketing / finance / project management skills that have been honed and perfected in the corporate world, can be transferred into any industry or role that you work in as an independent consultant or advisor.

5. You’re curious and a bit of a rebel

A huge part of portfolio careers is about being curious - about yourself, about others, and about meeting the needs of both!

If you’re constantly frustrated with being told that “this is how things are/aren’t done”, and having your ideas shot down or hampered by others then a portfolio career is definitely for you, and you will LOVE it.

One of the biggest push/pull factors for me back in my days of employment, was knowing what needed to be done for a project, being told my ideas were silly, and then having the project be resuscitated by my original idea... and not being able to say “I told you so” because, politics and politeness.

What frustrated me most was the people around me not being curious about doing things differently. So going plural for me was my way of rebelling against the straitjacket of the corporate world, striking out on my own, and getting my own voice out there. If this resonates with you, a portfolio career could be your calling!

6. You are comfortable with some discomfort

This is a key element to know whether a portfolio career is right for you.

A portfolio career is not all roses and sunshine, but it’s oh so rewarding. The difference between most people and those of us who want portfolio careers is that you’re comfortable with the discomforts that come with it. You might not like it very much, but you have the self-awareness and ability to see the silver lining, and resilience to wait for the sunshine.

There’s a reason I say some discomfort. Portfolio careers are perfect for you if want to start your own business, but never had that big, sparkly idea that VCs and other investors throw their money at. Being a founder of a startups is major discomfort - something I learnt by experience being second-in-command and a consultant at a few fast growing startups. It’s not for me, although the business skill set is similar.

If you’re being honest with yourself, you want the fun, flexibility and freedom, but becoming the next Unicorn is just not your thing - at least not yet.  

This post was originally published on Avalyn's blog: