Tag Archives: portfolio careers

How to Inch Towards Your Ideal Day

inchworm
Inchworm via Wikimedia Commons

Several years ago, back when I was contemplating a change in careers, I did an exercise where I described my “ideal day.” My description basically reads as follows: I spend my mornings writing, followed by some other, related creative activity: podcasting, giving a talk or interview, or attending a conference. The afternoons are devoted to a job that I love that brings home the bacon.

When friends call now – as they often do – to tell me that they’re tired of their job/industry/routine/life – I often begin by asking them to describe their ideal day. What I haven’t shared with them is that while my own description sits above my desk to remind me of my goals, I’ve not yet managed to achieve them. Most days, I write for an hour in the early morning and then do “real work” for the rest of the day. Sometimes, I start at 5 a.m. to squeeze it all in.

That changed this summer. With a bit more time on my hands, I slowly began to inch myself closer to realizing my ideal day. This didn’t happen magically; it was deliberate. Here are three changes I instituted that helped:

Saying No

One of the main upsides to running your own business is that you get to maximize the activities you like and minimize the ones you don’t. Otherwise, why not just go work for someone else who tells you how to spend your time?

Now that my business is up and running, I am fortunate to have a high number of repeat clients.  This means that I can spend less time selling and more time doing what I love – which is the design and delivery of workshops and coaching.

So I made a conscious choice this summer to considerably reduce the amount of business development that I do. Once I let go of cold calls, in particular, I suddenly had a lot more time in my day to devote to other things. Learning how to say “No” – as much to myself, as well as to others who were asking me to sell for them – was vital to this shift in behavior.

Taking Project Management Seriously

The second change I implemented was to get much smarter about managing my workload. I do a lot of work with universities, and the autumn tends to be my busiest time of the year for that work. So as the my calendar for the next few months begins to fill up, I am making sure to adhere to one of the fundamental principles of project management – which is to always work backwards from your deadlines.

The basic idea here is quite simple:  as soon as you have a deadline, work backwards so that you know exactly how much time you need allocate to that project each month/week/day etc. to hit it. As I tell my students, one important corollary to this old time management chestnut is to be sure that you block out your calendar to prepare for these deadlines. Otherwise, you’ll find yourself committing time to other projects and before you know it, you’ll be completely over-committed and stressed out.

It’s really hard for me to adhere to this principle, because my instinct is to always say “yes” and take on more work. But creating space to get “enough” work done and respecting that space is the only way to allocate time for other things you really value, like family, writing and exercise.

Embracing a Portfolio Mindset

I’ve written a lot about how I’ve embraced a portfolio career in later life. But a portfolio career is much more than a variety of different revenue streams. It’s also a mindset.

A portfolio mindset means that when you’re doing something that is part of your portfolio but not necessarily an income-earner – in my case, writing and volunteer work fall into this category – you don’t berate yourself endlessly when you’re spending time on those activities.

This was an incredibly hard transition for me to make. I’m very rule-bound. So if I decide that I will only spend one hour writing a day and eight hours “doing real work,” it’s really hard for me to break out of that routine.

But with more time on my hands this summer – largely due to Covid and its impact on my work – I found that I was better able to use my time to do a range of things that matter to me – even if I wasn’t earning money from them. The trick wasn’t finding the time. It was there. The trick was to re-frame that time as valuable and useful.

Writing with the wrong hand

All of which is a long way of saying that this summer I practiced what I call “writing with the wrong hand.” This is my shorthand for doing some things even when – and often especially when – they don’t feel comfortable.

My hope is that if I practice hard enough, some of these transitions will begin to feel routine. And then I will be that much closer to becoming my future self.

This blog originally ran on Sixty and Me.

Portfolio Careers: The Psychological Dimension

portfolio

portfolioA year or so before I broke up with my therapist, I arrived at one of our bi-monthly sessions one day, plopped myself down and announced that we’d be discussing career change. It was a few months after I’d been laid off from my job and I was beginning to contemplate my next professional move.

“I just don’t know how to pull it all together,” I moaned. “I mean, how do you combine writing, editing, coaching, delivering insight and project management all into one job description? What job is that?”

She looked at me quizzically. “Why would you want to do only one thing with your life?”

To paraphrase Buddha: “When the student is ready, the teacher appears.”

With that one simple question, my therapist got me thinking usefully about portfolio careers again.

 

The Rise of the Portfolio Career

Portfolio careers have been the new black for some time now in the work world. Technological change, flexible working arrangements, the demand for highly specialised skills and the evolving appeal of work-life balance mean that more people now have jobs that blend a number of roles. In the UK where I live, for example,  one in five British people are expected to earn money from a secondary form of employment by 2030.

Portfolio careers are proving particularly appealing with older workers, (a category in which I proudly count myself.) Precisely because we’re all living longer than ever before, there’s no reason for people to start working at 65 – or 75 for that matter!

And who knows how long current pension schemes will sustain us?

 

Diversifying Risk

Many workers, like myself, are pursuing portfolio careers out of economic necessity. As marketing guru Dorie Clark argues, it’s the best way to hedge against financial risk.

My own portfolio career as a communications professional comprises three main verticals, with a fourth in development. My main income stream comes from offering soft skills training of various sorts, principally in writing, speaking and blogging.

At the same time, I supplement my training work with a fair amount of editing.

I’ve also started work as a writing coach. This is a hybrid of the first two. It combines some of the line-editing and writing tips that come with being an editor, with the motivational aspects of the workshop facilitator.

Finally, I’m also training as a public speaking coach, a fourth income stream I hope to leverage in the new year.

 

Finding Balance

I think a lot of silverpreneurs embrace portfolio careers for reasons that extend way beyond our pocketbooks. As we age, portfolio careers also offer a greater degree of autonomy…and fulfillment.

In my own case, I’ve never fully managed to reconcile my manager and maker selves in one integrated whole. So doing a job that combines the deeply-focused, puzzle-solver of the editor with the animated cheerleader of the coach and the supportive nurturer of the teacher is a perfect blend of who I really am.

I’ve also come to realize that although personality tests repeatedly confirm that I’m an extrovert, there’s an introvert in there screaming (quietly) to assert herself as well. The introvert welcomes those days when she gets to stay at home in her pajamas poring over a text to make it read better. She doesn’t always need to be on the stage. She likes downtime and peace and quiet too. So that sort of balance is equally important to me in this new phase of life.

I used to think that finding the right career simply boiled down to figuring out what you like and what you’re good at and where those intersect. I now think it’s also about finding a job – or, more precisely, set of jobs – that speak to the different strands of your personality as well.

Image: Another pile of accordion file folders by Kasaa via Flickr