The 3 Career Investments Every Creative Should Be Making

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I am frequently asked for career advice, and I very, very rarely offer it.

Why? First, because I only intimately know my own path and those of a few others. Second, because all advice is local. What works for one person will be misery for another. Finally, when people ask for career advice, what they’re often asking is that you validate something they’ve already decided to do.

However, in the past few days I’ve been struck by stories of friends and colleagues who are feeling the effects of a shifting creative marketplace, and a decreasingly stable job market. Just like when the stock market takes a downturn and everyone gets very conservative, I see many creatives jumping at the first opportunity to come along rather than thinking about their career as an investment portfolio to be build over time.

With that in mind, here are three career investments that I think every single creative should be making now, and should continue to make consistently. These are the three aspirations that you should be chasing in order to ensure that you are positioning yourself to do increasingly meaningful and valuable work.

Flexibility of focus and engagement

In his excellent book So Good They Can’t Ignore You, Cal Newport argues that one major criterion for selecting a profession should be that it grants you increasing levels of flexibility as you grow professionally. He writes:

To construct work you love, you must first build career capital by mastering rare and valuable skills, and then cash in this capital for the type of traits that define compelling careers.

Rather than obsessing – as many do – on finding a job with an enjoyable set of tasks, try to negotiate for roles that will give an increasing measure of freedom of focus as you gain mastery. This will allow you to navigate your way into work that is personally meaningful and uniquely contributive.

This is a sticking point for many people. There’s a sentiment, especially on the web, that the goal is total freedom of time and place in your work. Flexibility is not the point, it is only the beginning. It exists to allow you to make the other investments.

Diversity of income

Are you completely dependent on one source of income? What would you do if that income disappeared next week? This is an especially dangerous trap for freelance creatives, who can become seduced by the comfort of steady income from a solid client only to have that income stream dry up when their internal champion at the company leaves.

Even if it means working a little extra time outside of work hours, or accepting fewer hours from a steady client, it’s wise to be diversifying your portfolio of income streams.

For in-house creatives or employees, this can mean starting to build something noncompetitive on the side as a hedge against future income disruption. Pam Slim calls these “side hustles”, and many great businesses begin this way. (If there is any chance that your employer would disapprove, it’s always a good idea to keep these projects in the open, but clearly separate from your workplace.)

You should devote a portion of your time each week to pursuing new income streams, or at least considering the present diversity of your income.

A final note: freedom to do meaningful work is connected to financial freedom. Many people increase their spending along with their incomes, and subsequently end up making tradeoffs along the way. As Lynda Barry once said, “The key to eternal happiness is low overhead and no debt.” (HT Austin Kleon) Just like you want to gain greater flexibility of focus over time, diversifying your income and living on less than you make gives you increasing flexibility to accept work that suits you well. Then, if all goes well, opportunity yields opportunity.

Building equity

Are you gaining a stake in your work? Are you building anything that will continue to hold value regardless of whether you continue to work?

One of the mistakes creatives often make is thinking only about income rather than also about ownership. They will happily accept payment for their services, then allow others to use their work to generate wealth. As you gain greater flexibility of focus and you diversify your income streams, you can begin thinking about engaging in activity that allows you to build something of your own rather than just supporting the efforts of others.

You should be devoting at least a portion of your time each week to building something you will own, whether on your own or in partnership with others.

Can you be sustainably successful without making these investments? Sure. Some people will be lucky enough to keep a steady job their entire career. However, in an increasingly unstable marketplace, my opinion is that you are far better off making these wise investments now so that you can reap a payoff later.

And again, all advice is local.


Die EmptyOne of the best books of the year. Passionate, practical and powerful, Todd will help you do more and do it better, starting right now.”
Seth Godin, author of The Icarus Deception

Available now! Amazon.com – Barnes & Noble – IndieBound


Todd Henry

Todd Henry

Positioning himself as an “arms dealer for the creative revolution”, Todd Henry teaches leaders and organizations how to establish practices that lead to everyday brilliance. He is the author of five books (The Accidental Creative, Die Empty, Louder Than Words, Herding Tigers, The Motivation Code) which have been translated into more than a dozen languages, and he speaks and consults across dozens of industries on creativity, leadership, and passion for work.

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