One thing they don't tell you about working for yourself.
The Portfolio Career Explained, Part 5
Five weeks ago when I chose the topic for today’s newsletter, I’d planned on writing a long list of “things they don’t tell you about working for yourself” that I’d learned over 5+ years of being self-employed. Things like:
You can sip a G&T on a sunny Tuesday at noon without anyone telling you otherwise
You can tell people ‘no thank you very much, I do not want to take that Zoom call’
You, and you alone, are responsible for dollars arriving in the bank before bills need to be paid
You can theoretically take a holiday whenever you please but typically never take a day off, as your business is all consuming like a demanding, petulant child
But as I started writing, I realised I wanted to share just one message that might be useful for those wanting to leave The Man and do their own thing:
Despite what people may say, you don’t need to quit your day job and go ‘all in’ to build the life you want.
Make the leap vs. take a step
There’s this misconception in entrepreneurship - whether it’s starting a business, becoming a solopreneur or building a career outside traditional structures - that unless you go all in you’re destined to fail. If you’re not all in, you’re one foot out. If you don’t throw yourself in the deep end, you’re not going to make it a success.
But going all in can feel out of reach unless you’ve got funding, a financially supportive spouse or a winning lottery ticket. Making a big leap thus feels both impossible and yet the only way forward.
And so, tangled in a web of our own indecision, we do nothing. We lie to ourselves saying “there’s no point in starting until I quit my job” or “I need a six month sabbatical to get things off the ground!” or “I can’t possibly start building on the side. It’s too hard, too scary, I’m too busy.”
We let our dreams of having a new life full-time, stop us from taking steps to create it part-time. We believe we have to make a giant leap and so paralysed, we don’t take the first step.
Ease in, not ‘all in’
Sometimes, for some people, taking a big risk and walking away from a salary is the right approach but it isn’t a prerequisite to putting the portfolio career wheels in motion. You don’t need to quit something before starting to build something else, nor do you need to let following your dreams undermine your ability to survive.
It doesn’t have to be all or nothing and in fact, this mindset is antithetical to the whole idea of a portfolio career, which is about creating a body of work and having income streams that come and go as your circumstances and goals change.
So instead of going all in, ease in. Dabble. Test and see what sticks. Grow your confidence, capability and perspective while experimenting and building on the side.
Easing in isn’t a cop out, it’s a strategy that takes advantage of the short term with the long game firmly in view. It doesn’t mean you’re not mentally and emotionally committed to the vision you hold for yourself. It doesn’t mean you’re not capable or committed or competent. It means you’re strong, clear and clever. It means you have a plan.
I don’t think there’s a single pathway to building a portfolio career but if there’s one thing I know to be true, it’s this: don’t believe you can’t do anything just because you can’t yet give it everything.
Because you can do something. You can take that first step. You can ease in.
And when you do?
You just might wake up one morning and find yourself all in, after all.
🎧 Listen to my thoughts on why the all in narrative is destructive AF
Also sorry upfront, I think I said the phrase ‘all in’ approximately 3000 times in this short clip. Please ignore where possible.
This post is part five of a seven 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. This post.
To portfolio or not to portfolio, that is the career question. Read here.
Some people are all in because they don't have much of a choice, like someone who recently got fired or laid off. However, you're right. If you have a relatively stable situation, it would be wise to ease into it and allow your full-time job fund your entrepreneurial venture.
This is smart advice! Thank you 🙏🏼