To portfolio or not to portfolio, that is the career question.
The Portfolio Career Explained, Part 6
A little note to those of you following along with this series: I originally intended to write seven newsletters about Portfolio Careers but alas, I’ve decided to stop at six. Why, you ask? Well, a seventh post felt like a stretch and I have a hard rule not to write something just for the sake of it, so I’m closing it out here.
Interestingly enough, it appears that by complete accident I’ve stumbled across a topic that I both love writing about and others enjoy reading. Quelle surprise!! My portfolio career musings won’t end here, and I’ll continue writing about building a business, career and life on my own terms. If you want to follow along, please subscribe.
Last week, I flicked open my inbox and was coolly greeted by an email written at 2:39am that morning from an evidently disgruntled and apparently anonymous reader, who wrote:
“I’m a founder and I just don’t understand people like you who want to build a one person business and nothing more.”
My heart rate stepped up a notch as I braced for criticism and maximum impact.
“It’s so fucking hard no matter how big or small your business is. I don’t know why people willingly go through the process of starting something if they don’t want to enact massive change in the world. It’s just not worth it otherwise.”
It certainly wasn’t what I expected to read before my morning latte, and after the initial shock of being semi-trolled for the first time evaporated, I became curious. While most of you (lovely readers) have shown overwhelming support throughout this series, some people simply can’t wrap their heads around a work structure that puts life first, and work second.
And to be honest, I get why they feel personally affronted or confused. A portfolio career is left of centre and instead of being clearly defined, it’s self defined, inherently challenging our thinking about what work “should” and could be.
I’m the first to admit it’s not everyone’s cup of tea. It’s not for the founder with a big vision and singular focus who wants to devote their whole life to solving an existential problem, nor is it for those who find comfort and joy in certainty, security and structure.
But while it’s not suited to all, it’s perfect for some. For those who want to challenge norms and disrupt spaces even if people think they’re weird. It’s for the misfits. The mavericks. For those who can park their beliefs and see through the looking glass to a different type of world - one where up is down, left is right, weekends are weekdays and nothing is as it seems. Where the systems and structures we believe are true and rigid and unshakeable, are malleable and can bend to our will.
It might sound chaotic and you know what? Sometimes it is. You have to be a Mad Hatter to join this party.
Curiouser and curiouser
There’s a reason most people don’t drink the portfolio potion - it requires you to think differently, act differently and change your beliefs about what’s possible. It also asks you to take a look at your motivations, values and skills to figure out if it’s right for you. If you’re considering this unconventional career path, here are some questions that may be useful:
Why am I considering this path?
I find it’s best practice to explore the deeper motivation when making a U turn in life. Do you want a change because you hate where you are now? Or are you looking to build upon your experience to create something even better?
What’s most important to me right now?
Values are constant but needs change over time. What’s most important to you in this very moment? Is it more money? More time? More meaning? More of a challenge? Is it less stress? Fewer commitments? Greater flexibility?
What’s my season in life?
This is a slightly different spin on the question above. Everything has seasons - Mother Nature, our lives and also our careers. Are you in a focused season? Are you in a learning season? A resting season? The season of ‘fucking around and finding out’?
Do I believe I have something valuable to offer?
As a multi-passionate, multi-strength human I’m sure you have a long laundry list of things that will provide value to others: whether it’s art (writing, podcasting, music), knowledge (industry or problem specific) or hard skills (task specific). Do you recognise your skills, talents, perspective and worth? If not, can you figure them out as you go?
Do I know that I can maintain the habits that will ultimately contribute to my success?
I’m a massive believer in focusing on habits and systems rather than exclusively on goals and dreams. What are the habits that will make your portfolio career a success? Are you already practising these behaviours? If not, why not? How can you quickly generate proof that you have the discipline to sustain them day after day?
Do I actually like working by and for myself?
One of the trade offs you may need to make is being part of a close knit IRL team. It can get lonely at times. There’s no water cooler gossip, there are no Friday night after work drinks. Instead you’ll probably spend a lot of time alone at your desk. Are you ok with that?
Do the people in my life support me in doing this?
You might be mostly working solo but you don’t have to go it alone entirely. Will your friends be there to listen when things inevitably get hard? Do you have a partner who can help carry the financial burden if things temporarily turn sour? How deep is your network, and who might step in to help you get things off the ground?
What are the opportunity costs?
What will you have to give up? A fancy title? Working for a cool brand? Status? Perks? Office chit chat? Having someone to learn from? Unique experiences? Leading a team? Some of these things might be hard to say goodbye to. Are you willing to do what it takes?
We’re all mad here
A year ago, after asking myself these questions (and many more) I decided to turn my back on amazing job opportunities, secure pay cheques and impressive titles in favour of creating my own body of work. To some people it made no sense because the upside was unclear, the risks were too high and the trade offs too great. But I saw things differently. I saw endless possibility and infinite potential.
Some people might call you mad if you start to venture down this path. They might email you anonymously at 2:39am saying they “just don’t understand” what you’re doing. It really doesn’t matter if they don’t get it though, all that matters is your belief that it’s possible and your commitment to continuing. No matter what it takes, no matter where it leads.
Down the rabbit hole you go.
🎧 Hear my late night deep dive into questions #3, #5, and #8
This is the final post in my six part deep dive into Portfolio Careers:
Saying cya to “traditional” work, and why I’m building a portfolio career instead. Read here.
WTF is a portfolio career? Read here.
How I’m building my portfolio of clients, projects and income streams. Read here.
Skills you need to run a successful one (wo)man show. Read here.
One thing they don’t tell you about working for yourself. Read here.
To portfolio or not to portfolio: is this career right for you? This post.
Just finished putting together a website layout for my portfolio, and I’m beyond exhausted. Funny enough, doing this for clients never felt this draining. After deciding to take a quick rest, your post was the first thing I saw on my phone. I managed to answer all your questions, and speaking my answers out loud reminded me why I started this journey in the first place. It dawned on me that the reason this feels so tough is because, while we're used to asking clients these questions to understand them better, I completely forgot to do this for myself. It's ironic how we can easily solve others' problems but struggle to do the same for ourselves. Thank you for creating this! Your questions helped me refocus and rediscover my original motivation, which was exactly what I needed at this moment. Now, back to the grind. 💪😁
People who think building a big business is just as hard as building a small business… simply have not done both.