Finding a Job You Can Do Remotely: Ideas for Those Switching Careers to Make Ends Meet

With COVID-19 reaching pandemic levels, the world is pretty scary right now; even scarier if you’re missing your paycheck while quarantined because your work can’t be done remotely.

For some, being confronted with just how “in-person” their job is was the push they needed to consider more remote-capable roles — office jobs, tech jobs, and others — that might offer more stability in a world that keeps changing.

As a management coach and talent leader that’s led lots of my own hiring processes and partnered with dozens of leaders on theirs, I want to give you some ideas on how to approach switching careers and be more competitive for remote jobs as an outsider to the industry and the work.

Start with the mirror. When money or job security’s an issue, our instinct can be to just pound out applications and resumes to as many open jobs as possible, hoping something sticks. In lots of great companies, hasty applications find their way to trash bin almost immediately. Do the opposite. Before you submit anything, or even edit your resume, take the time to think about:

• Where you shine: What skills or strengths do you bring to the table, that you frequently get complimented on? Are you better with people or with processes? Are you better selling or handling customer service issues? Are you good with learning highly-detailed technical tasks or terrible with detail? Your goal here isn’t a specific list of potential jobs, it’s a clear sense of the kinds of roles and experiences you’re looking for in your next job, and what kinds of roles would definitely not be a fit (e.g. I’d be great in a customer service role, and terrible in a data entry or finance role).
• How your current experiences might transfer in a different kind of job: Sometimes career switchers think too narrowly about what they’re qualified to do, because they focus on the specific context of the job and not the fundamental skills you demonstrated — which are usually applicable beyond your current kind of role. For example, my sister once sold luxury suits and watches in a retail store context. If she were thinking too narrowly, she might say “I know retail” or “If you put me in front of someone, I can sell.” Instead, she is now a rising star sales team member in a startup, working a phone every day to get potential members for her digital organization. How could she seamlessly make that job transition? Because context didn’t matter — her core superpowers, sales and building high-trust relationships quickly — would shine as well behind a desk as they did on the sales floor.
• What life needs you have that must be accommodated: it’s easy to think all office workers have it easy and work 8 hour days, unplug, then live our best life. There are absolutely some employers that value that kind of balance, but increasingly, lots of places expect that you are “always on” — especially for entry-level roles. Depending on what else is happening in your life (if you’re caregiving for others, etc), getting clear about what kinds of hours and workload you can accommodate and what kinds of benefits you can’t compromise on before you go too deep in your search can be helpful. I get that for some folks this is a luxury they can’t afford, but even knowing what your preferences are in terms of hours and benefits can make a real difference at the negotiating table and in terms of prioritizing roles to apply for.
• Know that sometimes the money or title is slightly lower than you’d expect to start out (but it doesn’t have to stay there). When switching to my first remote-capable role, I took a pretty significant pay cut (even after trying to negotiate salary — which you should always, always do). It isn’t always the case, but sometimes when you’re switching industries, the role you get hired for is slightly more junior or pays less than you’d prefer. If it’s in an organizational culture you can thrive in, if there’s growth opportunity, and if there’s a way you can make the salary and benefits work, I’d invite you to consider the role and not just dismiss it outright. I’ve since quadrupled my initial salary, and I know plenty of others who’ve done the same —it was a tough cut to manage, but if I’d stayed where I was for a few thousand dollars, there’s no way I’d be making what I make today (or as over-the-moon happy in my role!).

Less but better. Rather than cast a wide net, I propose you start your search with fewer but better fit positions. If you’re starting with 5 roles, you can customize your cover letter, resume, or any needed additional documents with a level of focus and care that just won’t be possible for 30 positions — and hiring managers can tell the difference.

• Spend more time searching. Now that you’re clear about what kind of work you’d be best at, dedicate some real time to searching and finding 3–5 positions you’d be jazzed about that seem roughly the right level for your skills and experiences. I’d also add a few “stretch” positions to this list — roles that are just beyond what you feel qualified for, but that you do show some of the key talents for. Prioritize this list in the order of your preference, and get ready to start applying.
• Refresh your resume, focusing on the skills that transfer. Create a resume using a template. When describing the jobs you’ve held, be sure to be honest, while focusing what you report on the skills and results that most directly transfer to the new role. For example, if you are a college student shifting from a barista role to a virtual assistant role, you might want to focus on your ability to manage a large volume of work — including up to 100 customers a shift in your busiest seasons. Feel free to include paid, intern, and volunteer experience, if needed. For example, imagine this student co-ran a visiting speakers event at their college that required her to keep impeccable notes and reach out to the assistants of high-profile people. That experience should absolutely show up on her resume!
• Don’t ditch the cover letter — customize it. Unless the employer explicitly asks not to include one, I’d recommend you include a cover letter with your resume every time. This is a simple, short document that speaks to who you are, why you want the role and to work for their company, and what about your experience and skills convinces you you’re a great fit. A well-written one can also differentiate you from the crowd. The key is you want to slightly customize it for every role — not just shoot off the same document. Aside from changing the position title and company name, I would also customize one or two lines in the paragraph where you explain why you want the job and in the concluding paragraph. Here’s an example I love.

Interview prep harder than you normally would. If you’re competing for a job that is a little less of an obvious jump for you, you’ll need to be prepared to awe your interviewer to stay in the running. To do this:

• Anticipate the questions they might ask. Although hiring managers like to believe our questions are super-unique, they’re often not (most commonly asked questions). Look at the job description and think like a hiring manager: if I were hiring for this job, what would I most need to ask about? Prepare answers to those questions. At minimum, I’d prepare to talk about your strengths and weaknesses, how you manage your workload/stay organized, examples of you hitting aggressive goals, bouncing back from a challenge, troubleshooting an interpersonal issue or communication challenge, and a time you made a mistake on the job/how you handled it.
• Craft tight stories to back up your answers — especially to the questions above: Any experienced interviewer is going to want you to prove what you say you’re good at. A well-crafted story from your work history is a great way to do that. The key is you’ll want it to be short, memorable, and a story that proves you can do what you say you can do. Ideally, you’ll want your story to take no more than a minute to tell, and to contain the situation, what you did, how it worked, and what you lesson you took from the experience.
• Come up with a compelling reason why your somewhat unconventional experience will actually be a win for the company. One of the questions you can expect your interviewer is asking themselves is “they’re from a totally different industry: can they do this job?” Being direct about why you see your somewhat unconventional path to the job as an advantage makes a memorable impact on your potential employer. For example, saying, “I can imagine that seeing someone with a ton of child care experience applying for a customer service role might be a surprise. I actually think my experience working with families, and troubleshooting lots of human emotion without losing my cool might be just what’s needed in a customer service role.” As a hiring manager, that’s not an answer I’ll soon forget.

Despite all the panic and layoffs around us, in lots of fields employers are still hiring. Here’s to hoping you’re able to use the tips above to find the right next role for you sooner and more easily than you thought possible.