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When’s the right time to quit your job and become your own boss?

A new breed of professionals are making the most of the digital revolution to take ownership of their careers. Instead of working for The Man, the gig economy makes it possible to be your own boss and manage a portfolio of jobs 

The digital revolution is slowly turning the clock back to greater individual ownership and accountability. ~Madhuri Sen

On any given day, Salman Saeed may be doing one or all of four different jobs. As a fashion blogger, he may be write about a new line of clothes or model some photos for his Instagram feed. As an internet designer, he could be in a strategy meeting at his web development agency. As a photographer, he could be creating content for brands. On a more personal front, he may be investing in foreign exchange and cryptocurrencies. “My typical week is full of emails with current clients, meetings with PR agencies and new companies for my web development agency, photo shoots for Instagram and analysing charts for forex and cryptocurrencies,” he tells Debonair.

“It’s my MacBook and me with a cup of green tea somewhere around Dubai in a café.” 

The 27-year-old Pakistani resident of the UAE is typical of a new breed of professionals setting out on starter jobs in the gig economy. Having come of age in the era of financial instability that followed the Great Recession, they dip in and out of home ownership, luxury car purchases and private equity investments alike. So why not do the same with their livelihoods? If a job is about paying one’s way through life, and work is meant to be enjoyable, why squander one’s best years working for The Man?

The digital revolution is slowly turning the clock back to greater individual ownership and accountability. ~Madhuri Sen

27-year-old Salman Saeed is among a new crop of professionals running a portfolio career. The Dubai-based Pakistani is juggling up to four ‘jobs’ at a time. 

The sexy term for this updated way of irregular employment is a portfolio career. In the US alone, more than 57 million people — or about a third of the total 160-million-strong workforce — freelanced in some capacity in 2017, according to research by Upwork and the Freelancers Union. By 2027, gig workers are expected to comprise more than half the labour force.

You may convince yourself of your own ability much faster than what the rest of the world is willing to accept. So get the training, certifications and even mentoring and apprenticeships if that’s what it takes

The situation varies around the world. Only 16 per cent of the EU presently freelances, for instance. Data is unavailable for the UAE; however, nearly all of the country’s 58 free zones offer some kind of freelancer visa for expatriates.

“The industrial revolution spawned a work culture primarily around large corporations and jobs. The digital revolution is slowly turning the clock back to greater individual ownership and accountability, even as aggregators increasingly displace corporations, and all types of entrepreneurs and freelancers displace employees,” explains Madhuri Sen, a consultant and business coach who, like her clients in the UAE and elsewhere, juggles a variety of jobs. 

Alice: “Would you tell me, please, which way I ought to go from here?” The Cheshire Cat: “That depends a good deal on where you want to get to...”

Lewis Carroll

Mike Lewis

The social entrepreneur was India country head for several multinational communications agencies and now heads three organisations concurrently, including the brand consultancy A.C.E Brand Strategist, the interiors firm Sites and Spaces and the lifestyle disease management practice Healthmode.Org

Rob Donker, a part-Dutch and part-Scottish Dubai-based fitness professional, dad blogger and model, says the biggest appeal of the portfolio career is the excitement factor. “It’s the adrenaline of trying to squeeze every meeting and training session into the day without being late,” the 30-year-old tells Debonair. 

“Of course there are benefits of ‘settling down’ as your future is stable, but where is the fun in that? There is a ceiling set out for you already; I’d like to have the opportunity to get through that ceiling by myself.”

Five years ago, author Mike Lewis, 29, who will be in Dubai this month as part of the Emirates Airline Festival of Literature, realised he’d be happier touring the world playing squash professionally than being a highly paid equity consultant. “The trouble is there’s no knock at the door; no one’s going to come in and say, now you can go chase your dream,” he told CNBC recently. 

With age working against him, he interviewed dozens of people who’d left something comfortable to live their passion, and eventually spent 18 months on the pro squash tour.

Lewis subsequently compiled those stories into a book, When to Jump: If the Job You Have Isn’t the Life You Want, which he hopes can serve as a voice of encouragement. He also founded a TED-style online community where people could support each other through the stresses of change.

Among those pain points is the fear that things may not run to plan, or that life’s responsibilities may get in the way. “I don’t believe that if you have kids and a mortgage or student debt to pay back today is the time to jump,” Lewis says. “But that doesn’t mean you can’t jump in a year or two years. We go through that in the book of how… [when] you get closer to when that time comes, you’re ready to go.”

To help the transition, then, Sen advises making like a boy scout. “I’d say firstly divide your life into needs and wants. The former lists all your living essentials, responsibilities, and liabilities — everything you can’t forego. Under the latter, the wants, put everything else,” she says.  

Then decide what you want to jump to, and assess if you have what it takes.

“Moving on from a set of core competencies and experience built over many years to a completely different set means having to build your professional credibility practically from scratch again. You may convince yourself of your own ability much faster than what the rest of the world is willing to accept. So get the training, certifications and even mentoring and apprenticeships if that’s what it takes,” she advises. “Last but not least, assess if your jump would be able to meet your list of needs at the bare minimum.”

She closes with a quote from Lewis Carol’s Alice’s Adventures in Wonderland. This is an exchange between Alice and The Cheshire Cat:

“Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to get to,” said the Cat. 

Mike Lewis is one of the authors attending the Emirates Airline Festival of Literature 

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