Dear Sophaya,
I’ve always commuted for work. I’ve spent the past five years at a great company, but the drive back and forth to the office is an hour and a half each way. That’s three hours of my day in traffic! I can’t take it anymore. I’ve been reading your blog and I’m really interested in working remotely, but to be honest, I have no clue where to start. I know quite a few people in my network who are working remotely. Should I ask them for help? Everyone says to leverage your network when looking for a job, but I feel awkward and I don’t know what to say. Can you advise me as to how my network can help me and what I should do to ask for that help?
Sincerely,
Awkward Alex

Wow, five years of that commute sounds exhausting! It makes complete sense that no matter how much you love your company, you’d be ready to make the switch to remote work. Long commutes are notoriously bad for your health. They’re frustrating. They’re expensive. And they cut into your valuable work-life balance. 

Your instinct to turn to your network is a great one. As you start speaking with people, you’ll quickly see that many of them took this same step themselves–and, more likely than not, lots of them probably found it awkward or uncomfortable at first. The fact is, a professional network exists as a support system to rely on in situations just like these. So keep that in the back of your mind as you enter into your initial conversations.

Start by reaching out to people in your networks who have remote jobs in your field that seem like they’re right in line with your dream opportunity. Let them know about the work you do, why you’re interested in remote work, what intrigues you about them and the work they do, and ask them if they’d be open to talking (either in-person, over the phone, over chat or via email depending on your shared availability and proximity to each other) about how they landed their gig and how it’s working out. Then, almost like you’d do in preparation for an interview, prepare a set of questions you absolutely want to have answered before you leave. Questions could include:

• How did you find your current job?
• [If relevant] How did you make the shift from traditional to remote work?
• How did you prepare for your interview?
• What advice would you give me on my search for a remote job?

Depending on how the conversation goes and how comfortable you are, you might even try asking if there are any open remote work opportunities the person you’re speaking with is aware of. 

Do you have people in your networks who work in different fields than you but at companies known for their remote work policies? They might also be great people to speak with. Ask them if they’d be willing to talk about the company and their experience. They might also be in the know about openings in other departments that could be a good fit for you. 

There are several other ways your network can be of use to you as well:

Secondary Connections

Reach out to people in your network to see if they are connected with any remote workers in your field that they’d be willing to introduce you to. Draft a template that you can easily customize to make outreach a bit easier. Not only will this expand your body of connections, but it will also open doors for opportunities you might otherwise have missed. 

Practice Interviews and Application Materials Review

Whether or not someone is a remote employee themselves, they can still be extremely helpful to you as you begin your job search. After five years at the same job, it’s very likely that your interview skills might be a little rusty, and your resume, cover letter, and LinkedIn might not be up to date. If you have friends or friendly professionals in your network who have experience in human resources (HR) or have conducted interviews in the past, politely ask if they’d be willing to practice interviews with you in exchange for coffee, dinner, or drinks. Ask them to throw in some questions about remote work, including why you’re hoping to make the switch, and ways in which you feel you’re equipped to work remotely. 

If you have connections with sharp editorial eyes, consider asking if they’d be open to reviewing your application materials (resume, cover letter, LinkedIn profile, or portfolio, for example). But remember: If they edit for a living and they aren’t a close friend, it’s polite to offer to pay them for their time–even if they ultimately decide they’ll do it pro bono. 

Remote Opportunities at Your Current Job

You mentioned that you love the company where you work. It might be possible to make the switch to remote work without leaving the place you love. Do you know of any coworkers who have any sort of part- or full-time remote work set up? If so, those are incredibly valuable connections to tap. If you’re comfortable with it, reach out to those coworkers and explain to them that you’re hoping for a remote work opportunity at your current company and are wondering if they have any advice. They may be able to help you negotiate a great remote work setup at your current job so you don’t even have to leave. 

It can feel awkward at first to reach out to someone you haven’t spoken to in months, if not years–but I promise: Most professionals have done it at some point during their career. If someone’s in your network, it’s likely they’re happy to hear from you, and equally likely that they’re happy to do what they can to help you take this next step in your career. Approach them with warmth, gratitude, and politeness, and you’ll likely leave the conversation with a closer relationship than what you started with. (And, soon, a remote job you love.) 

Best of luck!