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Career and Interview Tips

What It’s Like to Go Back to Work After a Long Break

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A version of this article previously appeared on Skillcrush, an online education program for creatives, thinkers, and makers that gives total tech newbies the tools to make major career changes.

Scott Morris, Skillcrush

About a year ago I started to consider getting back into the workforce. I'd left unskilled retail work and a long, meandering college career 12 years earlier to be an at-home parent to my first daughter. A second daughter followed three years after that—so I'd had my hands full trying to keep up with them while my wife worked full-time—but at the ages of 12 and nine, my kids were getting to a point where they didn't need as much constant parental care. Meanwhile, my wife and I were looking for ways to add some savings for their college funds, and to have extra money set aside for emergencies.

The problem was, my parenting duties were still just enough to make the idea of working outside the home—even part time—fairly daunting. I remember thinking that if only there were a way to make money from home, that would be the perfect scenario—but the idea sounded like something out of a get rich quick scam. Fortunately, I told my woes to a friend of mine and she metaphorically slapped some sense into me about the very real, very achievable world of remote work. The company she worked for happened to be looking for part-time copywriting help, and within a couple of weeks of our first conversation, I found myself working for Skillcrush.

At the age of 40, I thought I'd run my course as far as what I was going to be doing with my life—I've never been a particularly ambitious or career-minded person, and I was perfectly happy with most aspects of being an at-home parent and husband. But, I did still feel like something was missing. It had been so many years since I'd really gone out on a limb and tried something new that there was a part of me that felt stagnant.

Paid work filled this void by adding a new dimension to my life, and—although I'm busier now than I've been in years—my life is fuller and more focused than it was before. I have to think about schedules and parcel out specific time for different activities in a more regimented way than I did before, and it makes me really think about how to spend my time and appreciate the downtime I have in between. It's also refreshing to learn and implement new skills—and actually earn a paycheck for doing so.

I'm Not a Barista Anymore: Fighting Impostor Syndrome

At first, I looked at my new job the same way as the bookstore and barista jobs I'd had decades prior: I figured I was supposed to be available, receive instruction on what to do, do what I was told, and rinse and repeat. I worried that asking for clarification or even requesting more work would be perceived as me not knowing what I was doing and expose the fact that I really didn't belong. But professional work isn't about clocking in and mindlessly following a set of instructions—you need to find or create opportunities to get actively involved in your workplace, particularly if you're freelancing or remote, where nobody actually sees you.

And, I needed to let go of my impostor syndrome. If I didn't belong, they wouldn't have asked me to be there—end of story. But I let that feeling take over, afraid of my own shadow, sitting quietly and not wanting to be noticed as opportunities passed me by.

With that approach, my hours dried up and I was exactly where I was before: stagnant. Luckily, a few other Skillcrushers were kind enough to clue me in on how things work. Asking questions? Not a bad thing. Requesting more hours and seeking out ways to evolve and define your role as a part-time freelancer? Also not a bad thing. Once I followed this advice, I started to hit my stride and establish a solid role in the company.

Here's what I wish I'd known when I started: Don't be afraid to express interest in projects you're not already attached to, or to let your managers or coworkers know about skills or interests you have that aren't typically part of your job title. Try saying something like "I hear that we're developing a podcast. I have some audio editing skills and I'd love to be a part of the project." Or, "I'd love to learn more about how we track our audience. May I sit in on the next numbers meeting and observe?" Nobody will think you're being pushy (my greatest fear). Remember that your colleagues and managers want you to succeed—and if they don't, you're working for the wrong company.

More Work is a Good Thing?

Beyond learning the culture of a workplace, I also had to adjust to an entirely new system of timing. During my first few weeks of working for Skillcrush, the extra hours of paid work didn't have much of an impact on my unpaid work of housework and childcare duties—until one particularly dark, rainy day when the dishes had piled up, a chimney leak was letting water into the living room, my kids had an early release day from school. . .and I had an article due that I hadn't even started yet.

At the time, I'd banged out my first few Skillcrush articles without really knowing what I was doing. I started at Skillcrush in the middle of the holiday season and bounced between different roles before settling into my current place on our editorial team, so I didn't have an official, black and white training period. This—combined with my overall lack of experience—turned each article I wrote into an anxiety-laden experience. Whenever I finished writing I felt like, "Oh thank god! I finished it, it's over! I don't have to do that again!" But—of course—this was a job, and after one article was finished, the next one needed to be done. And this particular rainy day was the first time my mounting anxiety partnered with my backed-up domestic duties to make the whole thing feel impossible.

I remember totally freaking out: "WTF have I gotten myself into? There's no way I can get everything done!" But after a few deep breaths I started the article, took a break to pick up my kids, finished the article, and excavated the dishes. The leak got fixed about 6 months later, but the point is: There was time to do it all—I just had to focus on one task at a time, and everything started to fall into place.

In the months since—whenever my schedule starts to seem overwhelming—I think back to the methodical approach that pulled that day together, and it makes me remember that the focus of having part-time remote work on top of my domestic duties actually makes me more efficient all around. There's a greater feeling of urgency to get everything done, which means there's less time spent procrastinating and avoiding—I literally can't get away with putting things off anymore—and that's been a positive change in my life.

What's the Plan?

That said, I have had to be proactive in my new, efficient life back in the workforce. Paid work is a whole new world—particularly if you've been out of the game for awhile. You have to learn the ins and outs of how your workplace functions, navigate a new set of social interactions, calibrate your ability to meet deadlines, and (if you're working remotely) remember to change out of your pajamas in the morning. It took me a few months to get used to all of this, much less to get to a place where meetings and reporting to managers didn't automatically fill me with dread—not based on anything anyone else was doing, but just due to my own feelings of inexperience and insecurity. The ability to figure all of this out and still get work done doesn't come together accidentally or automatically. It's all on you to establish systems and habits that will help you succeed. I learned this the hard way.

For my first couple of months I had a completely scattershot approach to working—no plan for when I was going to work, no breaks built-into my schedule (because I didn't have a schedule), entire days spent forgetting to drink water or eat anything—and I was starting to feel completely rudderless and out of control.

I'd start my day intending to do paid work, but then I'd notice some things that needed to be done around the house and I'd decide to take care of those first. Of course—en route to doing vacuuming or laundry folding—I'd put off making coffee or eating breakfast, but after a few hours of chores I'd realize the day was slipping away, so I'd absent-mindedly sit down at the computer, "just to get started." Four to six hours later, my paid work was done, but I was totally fried and wrecked going into the next day where I'd begin this haphazard run all over again.

This approach obviously wasn't working, so at a certain point I had to take a time out and reassess—I'd read all the articles and seen the advice about how you need to create structure when working from home (schedules, breaks, an environment conducive to getting work done, etc), but I'd kept telling myself I'd get to it eventually. The truth is it's all stuff you need to address on day one (or if you're past day one, then right now).

In the months since, I've adjusted my approach—the night before a work day I make sure the house (or at least the area I'm going to be working in) is clean enough so that I'm not distracted, I put off all non-essential housework during the day until I'm done with paid work that's due (or that I've scheduled to get done that day), I keep a written log of what I'm working on in Google Docs, I add due dates to my calendar, I mindfully schedule when I'm going to do what, and I try to stick to the same routine every day as best I can. The results of this approach have been night and day—I now feel like I have a handle on what I'm doing, and I'm able to maintain physical and mental health while also working and caring for my house and family.

In my year at Skillcrush, I've had my eyes opened to how many opportunities there are—not just for work in tech—but for quickly gaining the skills needed to start new careers. I always thought that starting a new career would require years of school and certifications, and that's just not the case. In interviews I've done with tech professionals and conversations I've had with Skillcrush alumni, I've been surprised at the number of people who were in similar situations to mine, and how many success stories there are when it comes to remote work, online coding classes, and other non-traditional venues as a path for returning to the workforce.

I worried about the adjustment, too, but that also fell into place (with some proactive but manageable work on my end), so if you're looking to add paid remote work to your domestic work as a parent or an at-home partner, don't let the extra hours and duties intimidate you. You'll likely find that the tension between paid work and other responsibilities will actually make your days more focused and efficient.

And maybe the biggest bonus is one that was totally unexpected: At a time in my life when I was set in my ways and thought I'd met just about everyone I was ever going to know, I've been introduced to a whole new cast of smart, funny, creative, inspiring people, all while learning new things every day and getting paid. I'm not sure how it gets better than that, and now that it's so integrated into my life, it's weird to think that this part of me didn't exist just a year ago.

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