Figuring Out What’s Next

Sometimes to know where you want to go you need to think more about where you've been

Sometimes, before you can know where you want to go you have to figure out where you are and where you’ve been. Photo by Annie Spratt on Unsplash

The last time I was unemployed, in 2003, I was trying to land another job in media. I had started my career in book publishing but moved into online media, first at iVillage then at News Corp. where I got laid off. Surviving two years of escalating layoffs at a tech startup only to be laid off after 6 months by one of the world’s largest companies was a low point in my career. It also made me realize that there’s no such thing as a safe bet – everything is risky.

I was open to going back to books, under the right circumstances, but was also looking more broadly across different types of media, both online and traditional. I was looking at women’s magazines, all of which were building or expanding online content making my experience at iVillage seem especially relevant. 

I experienced a bunch of tough moments during that search – many that made me question if I’d ever work again. I had an interviewer tell me that I should stop talking about my time at iVillage because it was “a failed business model.” (For the record, iVillage went on to be acquired by NBC Universal and would live another decade before being shut down in 2013.) I lost out on three jobs to candidates who I personally knew. I felt like the walls were closing in. 

But a moment that popped into my head recently, as I continue to figure out where I’ll be welcome and where I’ll be wanted, was an interview I had at MTV. The HR woman, who never advanced me past that initial meeting, said “You should know that at MTV we don’t pay well. We don’t have to.” Well, okay. Noted. 

Around the same time I was at a networking event and I met the editor-in-chief of one of the most prominent food websites –  Epicurious.com, I think? Maybe Gourmet.com? In any event, I walked up to her and said, “You have my dream job.” She paused, looked me straight in the eye and said “You should know that your dream is a nightmare.” 

Too many talented people chasing too few jobs is a recipe for a frustrating search with low pay and terrible jobs as a reward. As the saying goes, “Play stupid games, win stupid prizes.”

I’d like to tell you that I finally landed a job by being strategic and planful in outlining my transferable skills and networking my way into a shiny new job. But that would not be true. What actually happened was that I impulsively applied for a job as a part-time email newsletter writer. I figured some income was better than no income and I could continue looking for the right full-time role. That application led, strangely and improbably, to a role at a software company that lasted for more than a decade. I do believe that my mindset shift helped me be open to new opportunities and say “yes” to a job that wasn’t like anything I’d previously considered.

I’m now looking for a job for the first time in more than 20 years. And I’m finding myself in what feels like a similar situation to the one I was in back then. I’ve been focused on applying for roles that, on paper, I should be a strong fit for. But the market is fierce, nonprofit jobs are highly desired, and my experience doesn’t seem to be compelling. 

I’ve been focused on roles at nonprofit organizations because I truly loved the work I did at Path Forward. Empowering caregivers, especially women, to return to their careers was a great joy. There is purpose and meaning to be found in working toward an important mission. 

But I’ve also focused on those roles because I know that it’s often easiest for people to get a job that is most similar to the one they most recently had. Convincing people you can do something you haven’t done, or haven’t done very recently, can be tough. For example, during my 2003 search, I interviewed with an executive at HarperCollins who noted that they’d have to teach me book publishing “again.” At that point I’d been out of the book industry for two years. Focusing on jobs that are extremely similar to what you just did is often much easier, and faster, than trying to pivot.

But it’s not quite working out that way for me, which means I need to take a new approach. And while I’m always open to serendipity, I think I need to be a bit more strategic and planful than I was back in 2003. I’ve now had three pivots which means my 30 years of professional experience is chopped up into chunks of roughly a decade each. My resume is hard for anyone to make sense of. And, if I’m being honest, it’s hard for me to even know what kinds of roles to focus on. 

So with all that, here’s what I’m doing now:

1. I’m creating a skills map. I’m breaking apart my resume to pull out the specific skills that I gained or refined in each role. And then I’m rating each skill by how much I like doing that thing. It’s funny, because this is advice I gave at Path Forward all the time. Don’t include stuff on your resume that you don’t actually like doing! But it’s been hard for me to let go of experiences that I think are desirable in the market.

2. I’m networking. I have been doing a lot of networking since I left Path Forward, of course. Goodness knows that is a gospel I preached a lot. And I’ve been networking in a way that seemed most efficient and effective – finding connections to organizations I was applying to, and asking for referrals. But that approach has not been effective for me so far. Once I’ve completed my skill map, I’m going to share my findings with some folks to see what ideas other people have about what kinds of roles might be a good fit for me. 

I think this exercise will help me to more fully understand – and tell others – what kinds of roles might be a good fit for me now. 

When I finish my skills map I’ll write about it and also I will create a downloadable version if you want to do this exercise for yourself. Looking forward to seeing what you all come up with!