Ask Career Contessa: How to Make a Major Career Move (and Other Questions)
Interview by Tyler Calder
Making a major career move? Let us be the first to say we’re proud of you. Shifting gears can be terrifying, so it’s no surprise that the GNI team often gets questions about how to navigate new career territory while maintaining some semblance of balance and self-care.
In the spirit of our January theme of self-investment, we brought in an expert, Career Contessa’s Kit Warchol, to answer some of the biggest questions we all have when considering a career pivot, new opportunity, or complete change of career scenery. Here are some snippets from our Q&A:
What does the roadmap for making a major career change look like?
This is a tough one because, while there are definitely a few techniques that everyone can use, it depends entirely on the person. When you feel pull-your-hair-out-and-cry-every-Monday-morning stuck, it makes sense that you’d want to head straight home after work to binge on the latest Netflix miniseries or Cheers reruns, but that’s the opposite of what you should be doing if you’re ready for a change.
That can mean taking an online class, emailing your network to see if anyone knows someone you can talk to in XYZ industry, or even just asking ten of your friends what jobs they think you’d be good at. I’ve done that last one and it’s insanely enlightening (just don’t take it the wrong way if one of the jobs is out of left field). Any move is the right move and usually leads you directly to a next step. And beyond that: Trust your gut and say yes to everything you can.
What resources exist for taking such a leap?
When you’ve been working in an industry for a while and want to make a big switch, the most useful resource is one-on-one career counseling. You see a therapist when you need to get a handle on a failing relationship or mounting social anxiety, so why wouldn’t you talk to an expert when you need help with your work and career? We have a service called Hire a Mentor that lets you book sessions with various women in different fields and industries. Talking to someone who knows the industry is key because they can give you honest feedback on how to tweak your resume, cover letters, and more.
If you’re more of an Abraham Lincoln-style (Baberaham Lincoln??) autodidact, there are plenty of podcasts and books out there as well. I love the podcast Help Me Be Me (which has some incredible episodes on career stuff), the book You Are a Badass (don’t be put off by the insanely embarrassing looking cover), and Ahyiana Angel’s Switch, Pivot, or Quit podcast.
How do I find a mentor in my desired field? It feels like it’s a world away from my current job.
Two magic words: informational interviews. If you take one piece of advice away from reading this, please let it be “I need to book one.” Informational interviews are a way to talk to real people doing the work you want to be doing.
Here’s how they work: Do your research and connect with women in your desired field either through your own network or by reaching out on LinkedIn. Ask them if you can speak to them for 20 minutes by phone or even meet for a coffee if they seem receptive. When you talk, do not — and I repeat, do not — ask them for a job. This isn’t about that. It’s about learning about what they do and getting insight and advice. Afterwards, stay in touch consistently with them through LinkedIn and see what happens. Ask them to another coffee date a month or so later. Build that bond. It works — Career Contessa’s founder did dozens of informational interviews, which led her to quit her education-world job and join Hulu as a recruiter.
How do I get a sense for the work-life balance/lifestyle adjustments of a new industry?
This is a great question to ask in those informational interviews. The people who know best are the ones who are doing it, right? And once you’re in the job, you’ll obviously want to watch what your coworkers and, more importantly, your boss does and adapt accordingly.
What do I do if my dream job requires me to move to a completely different place?
Pop a bottle of Prosecco and celebrate! But in all seriousness, this is a huge opportunity to totally reinvent yourself, and you’re going to be just fine. Worst case scenario: You wind up moving back. So what? Especially if you’re kidless, don’t own a home, and have some years ahead of you, the risk isn’t that great.
And even if you do have kids, it’s not off the table. My parents did it when my mom was 7 months pregnant, again when I was four, and again when I was 12. I think I turned out great. And if you’re worried about friends, ask your network if they know anyone in said city and set up some blind “dates.” Two of my best friends today did this when they first moved to LA, and lo and behold, after sitting down for a drink with each of them way back when, we’ve been inseparable since.
How do I handle feeling entry level in a new field when I know I’m not really entry level in professional experience?
For starters, stop calling yourself entry level. Most, if not all, of the skills you have currently can benefit you in the role you want to get into. Tweak your resume, cover letter, and LinkedIn to make it clear that your current job has some serious parallels to the work that you want to do.
Also, figure out what your skill gaps are and start filling them now. If you know the job you want will involve using Google analytics, take the free courses they offer online! In your interviews, you can mention that you’re in the process of learning the skills you need that aren’t on your resume yet (which is very self-starter of you). Who doesn’t love a self-starter?
How should I ask about company culture in an interview?
The most obvious — but effective — one is, “Could you tell me a little about the company culture and who I’d be working with?” I also always like getting questions like, “What did you like about the person who previously held this role? What would you like me to do differently?” as well as “How do you see this role evolving within the company over the next few years?” But maybe more importantly, read the room while you’re there. It will tell you much more than you think. We wrote a whole article on how to recognize a toxic company culture from the interview, now that I think of it.
What if I feel too old to completely change course?
First of all, you’re not. My mom (who is the O.G. working-mom-feminist-go-getter) just changed her career path for the fourth time at 60. She pulled this off because: 1) she’s the queen of networking, although she would just call it “making conversation” and 2) she’s not afraid to learn new things that come her way. Last week she texted to ask me, “How do you use Instagram stories to reach your audience? I want to do something like that at my work.” She’s also really good at explaining how her past work can fit into a new industry when she walks into interviews.
That being said, if you don’t want to make such a big shift (or aren’t OK with the risk involved in terms of a possible financial or professional setbacks), you could try shifting your role within your current company or moving laterally within your industry. Bosses are always open to hearing your ideas for how you can get involved in some new projects outside of your normal responsibilities. Or hey, start a side project and see what happens. It’s amazing how rejuvenating just doing something new (and preferably uncomfortable) can be.
Published in partnership with Career Contessa.