Thinking Of Ditching Your Job To Work-From-Home? Here Are The 7 Things You Should Know

For all the changes stemming from the intrusion of Covid-19, the relocation of our offices to our living rooms and the normalization of non-working-norms is a big one. That’s not necessarily a bad thing. In fact, for some of us, it’s turning out to be just the ticket for gaining more control over when, where, and how we work—not to mention on what and for whom.

Has the experience of working from home tempted you to think of switching to a portfolio career, one in which you chart the course and call the shots? While the gig economy isn’t new, it has been thrust into the spotlight, thanks to this year’s mass experiment in working from home. With flexibility and choice as its strongest selling points, many are tempted to hop aboard the gigging juggernaut, but as seasoned giggers will tell you, the ride is often far from smooth.

I made the switch to a portfolio career—trading in a corporate job for a combination of speaking, consulting, teaching, and board director roles—at age 37. Going in, I was clear about what I wanted in my personal life and career, which was flexibility in terms of time and the ability to live on both coasts. I’ve never regretted the decision. That said, it’s certainly been a learning experience, and there are more than a few key things I wish I’d known before making the switch. 

Some people like having structure and routine to their work. For me, the diversity of a portfolio of various projects and jobs was more compelling than the stability and predictability of a single role. I always took exception, however, to people asking me when I was going to go back to work “full-time,” because the first lesson you learn as a gigger is that the work can be full time—and then some. 

So before you opt for a work-from-home career, run out to stock your home office and buy the celebratory champagne, know this: A gig lifestyle isn’t for everybody. For sure, there are incredible upsides, but there are also plenty of counterbalancing factors to bear in mind. Here are a few things worth considering before making the leap.

1. Your Calendar Will Fill Up Fast

You may be in for a surprise when you see how busy you can be working part-time on several different jobs. Despite my warning them in advance, many of my operator-turned-board director colleagues can’t believe how quickly their days get filled in. They often wonder how they managed to do all the things they’re doing when working a “full-time” job! 

2. There’s No IT Team To Call

Many people don’t realize how much they’ll miss their support staff until the first time their computer freezes up and they have no IT team to call. You’ll need a gameplan to compensate for the lack of corporate infrastructure you’re used to. Fortunately, whether it’s virtual assistants or on-demand support services, there’s a growing plethora of support infrastructure available to freelancers and giggers. 

3. You’re A Leader With No Team 

If you’ll miss working with and leading a team, think long and hard about leaving that behind. For many leaders, the positive impact you can have on someone’s life and career is one of the most gratifying parts of the job. Going solo deprives you of some of that opportunity and equally means forgoing for yourself the mentorship and advice on hand daily from a boss and colleagues. 

4. There Go The Perks

Ditto the validation from the boss. When you’re on your own, you have to learn how to pat yourself on the back for a job well done. You also have to watch out for your mistakes and vigilantly try to learn from them, which is harder to do in the absence of feedback. And those sales recognition coastal retreats and year-end bonuses? They’re also on you.

5. Cash Flow Is Real

Even for well-established giggers, managing cash flow can be an issue. Especially when starting out—when you’re building your portfolio—it’s a good idea to have a cushion to fall back when you know the paycheck isn’t guaranteed on the first of every month. Sending out invoices and chasing down payments is definitely one of the less-sexy sides of gigging, but it’s a reality nevertheless. So too is being fiscally prudent and managing your personal burn-rate. 

6. You’re A Small Business Owner

This raises a broader point. As a gigger, you’re really less of a lone-ranger than you are a small business owner. It’s non-trivial to have to figure out your health insurance, when corporate subsidies are no more, or ensuring that your tax estimates are filed quarterly and accurately. A smart tactic is to put the proper processes in place with support from the right experts from the get go. 

7. You Just May Love It

If all of the above sounds like bad news, fear not. The plus side is that the flexibility is amazing. You decide what to do and when to do it. This is your project, and you are the director. No more looking at your schedule with dread because of back-to back meetings you’re obliged to attend. Gone too are the office politics, expensive dress codes, and long commutes. It’s hard to put a price on being able to quit your desk for a half hour to shoot hoops with your kids without having to answer to anyone. 

The most important thing to know before making this, or any other kind of career pivot, is exactly what you want from your life and your career at this juncture. Pick the one or two things that you’re solving for and stay relentlessly focused on them. If gigging or a portfolio career brings you closer to those things, then it may be just the ticket to a future that’s shaped around your desires, passions, and priorities. 

Before you pack up your cubicle and hang your own shingle out, it’s helpful to know the realities that await and that the grass isn’t going to be entirely greener on the other side But then again, if you subscribe to the notion that the grass is greener where you water it, then the gigging life might well be for you.

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