Perspectives on the Future of Work: April 11

Upwork’s weekly column brings you the latest news on hiring and working with freelancers, freelancing, and the future of work.

Forbes | How to Have Two Successful Careers at the Same Time

The future of “moonlighting” has a new buzzword, reports Forbes contributor and author Ruchika Tulshyan. Alongside the rise of independent contractors and solo entrepreneurs, there’s a growing trend toward “portfolio careers”—where professionals maintain a full-time career while pursuing secondary part-time roles or freelance projects that align with their passions and interests.

Rather than being viewed as an escape plan for transitioning out of a career and into a fully freelance lifestyle, these secondary careers provide additional income, fulfillment, and flexibility, she says. “More millennials are seeing their career trajectories shaping up more like a jungle gym than a straight career ladder, where multiple self-directed activities could lead to a self-created version of career success,” said Tulshyan.

Portfolio careers can be viable over the long-term with some care, according to consultant Samantha Clark, who shares a few tips for anyone considering taking this approach to their work life.

Careful planning is key. “It’s important to have a portfolio plan that maps out your cash, lifestyle and skills,” she said. “I don’t advise quitting a full-time job without mapping all of this out.”

Find the complementary pieces and fit them together. “Is there a way the different pieces of your portfolio career could overlap? Are there skills you could develop in one area that could be handy in another?” says Clark.

Schedule your time in advance. “[P]eople get burnt out by not planning their schedule properly…It’s easy to find lots of shiny new things and take off in different directions.”

Co.Exist | This Company Wants To Make Tax Season Easier For The 1099 Economy

Tax time is rarely a treat for anyone, but freelancers frequently face a much more complex level of challenge when it comes to taming their annual taxes. A new company aims to remove the sting of seasonal tax woes, however, by offering banking options that include smart savings accounts that auto-deduct enough earnings to cover estimated taxes, reports Co.Exist writer Ben Schiller.

Painless1099 caters heavily to the growing freelance population, with a service that tucks away the appropriate percentage of your income for taxes as soon as it comes in.

“Where most people get in trouble in the 1099 world is in managing their tax obligations,” said Painless1099 co-founder ACe Callwood. “The American workforce is terrible at putting aside 15% to 20% of their money and not pinching into it for various reasons. This is about getting money out of your face before you see it and want to spend it.”

HOW Magazine | Insights from a Rocky Road to Creative Self-Employment

Transitioning from full-time employment to the freelance life can be tough if you don’t have the time to plan and build a runway to ease into the flow of self-employment. HOW guest contributor and freelance designer Greg Paprocki found himself in that very predicament after losing his agency job and setting out on his own. The sudden shift in gears proved to be a difficult one, he says, but it ultimately led down the path towards a more fulfilling career as a freelance designer.

“The best professional decision I ever made was to forgo relaxing after work and on weekends so that I could build my portfolio. I would come home from my job and get started on my book or anything else that would bolster my body of work,” he said. “Beefing up my body of work with art that had a very wide degree of styles gave me an edge.”

This helped Paprocki secure work almost immediately when he made the move to freelancing, and it’s one of many tips he offers to prospective freelancers. Additionally, he suggests that self-employed creatives keep up with current industry rates to avoid undervaluing their services, take steps to protect their intellectual property rights, and remain flexible when working with clients.

What changes in the workplace have caught your attention recently? Tell us about them in the comments below!

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