How to listen for the clues

Getting stuck along my journey of finding a job with meaning was the best thing that could’ve happened to me (in retrospect, of course).

During that time, some guardian angel recommended What Color Is Your Parachute, and another the new-agey yoga retreat center Kripalu. I am eternally grateful I had the opportunity that summer to go to a workshop at Kripalu about life transitions, and to dive into that book – both of which were instrumental in helping me see what really mattered to me, and to envision (in quite a lot of detail) what I wanted to do with my life, who I wanted to be surrounded with, and even what I wanted the office to feel like.

Now, I had lots and lots of clues…

However, these clues didn’t spell out how to actually find the right job – there wasn’t a particular cause I lived for, or a specific role I felt called to do. I didn’t understand it at the time, but I was really a generalist – fairly good at a wide range of things, and especially at bringing different things together. But that made it harder to find anything that felt like a good next step!


Even though all those exercises and reflection helped me build more confidence and clarity in what mattered to me, it took many more months to effectively narrow my search – and more months after that to actually get the right job.

It wasn’t for lack of trying – and in fact, I think my ability to keep trying was critical to understanding how a search process can work.

But first, I had to deal with applications that went nowhere, interviews that felt awkward, and eventually settling for temp jobs – first, handing out pamphlets at a trade show, and then (at least getting closer) as an administrative assistant for a large nonprofit.

With a secure job finally in place in November, I took a breath, but it wasn’t long before I realized this very old, national nonprofit was way too bureaucratic for me, that my skills weren’t really valued, and that the staff wasn’t treated particularly well. So I went back to my Parachute instructions, and started working my connections for more informational interviews in the nonprofit arena, now having more clarity about the type of organization, or the culture, that would be a better fit for me.

These clues – about where and how I wanted to work – would be game-changers.

The people I met with were genuinely willing to hear about what I was looking for, to share what they knew about the nonprofit sector, and to introduce me to other people they knew – because (I imagine now) they knew that finding great people was a challenge, and they wanted to do what they could to make connections.

It was one of those connections who had a job posting on his desk from an organization that was opening an office in Chicago, and who made an introduction for me. By February, that turned into a job opportunity I was really excited about, and an interview I felt great about… and then, a job that I didn’t get. I was crushed.

I took some time to process and grieve – I had done all the right things! I had clarity on what I wanted and what I was good at, had used all my networking skills (even though I am an introvert and networking is hard!!), and kept meeting with people… and it didn’t work out! And in the meantime, the job that I actually had was getting worse – more mindless, with more turnover in the organization, and a fax machine behind my desk that was straight out of Office Space. I felt stuck. Again.

landscape photography of orange brick wall
Photo by Mikes Photos on

A few months later, I got a call from the organization that had rejected me so heartlessly, offering me a summer internship. That almost felt worse… I was now almost a year out of college, and my best prospect was a paid internship, with no clear sense of whether that could turn into an actual job.

But, I had really loved what this organization was doing, how they were approaching the challenge, and the way they welcomed creative thinking and leadership from everyone. The opportunity to do something that better aligned with what mattered to me made it worth the risk. That May, I quit my job and took the internship.

What is a risk – whether small or big – that you could take to move you closer to what you seek?

action active activity adventure
Photo by Anthony on

What do you want to be when you grow up?

Almost 20 years into my career, I’ve reached a place of clarity on my passions, my strengths, and how I can contribute to the world through my work.


Now that I’ve built deep experience on all sides of the hiring process – from trying to find the right fit for myself, to being that HR person reading resumes, to consulting with organizations to help them find the right people, to coaching individuals who are wanting to switch careers or step into more challenging positions – I know the hardest aspects are really knowing what you want, and then figuring out how to get it.

We might work through lots of personality tests, exercises in books, core competencies of jobs, or stacks of resumes. But in the end, finding the right fit is much more art than science, and usually takes time and stepping out on faith that the decision you make is the right one (for right now, at least).

I know this in my bones – because I’ve been there. I’ve held a number of different jobs with different organizations (and worked for myself), consulted with 50+ organizations, hired for well over 200 positions, interviewed close to 2000 people, and read through many thousands of resumes.

But the path I’ve taken hasn’t ever been straightforward – nor did I have any real sense of direction for a long time.

The answer to that (really annoying) question, “what do you want to be when you grow up?” was never clear to me.

afterglow backlit beautiful crescent moon
Photo by luizclas on

In high school, I was friends with people who were already great at something – music, poetry, science, math, theater. I was okay at a lot of things, and not great at forcing myself to work really, really hard to get an A in any of them. I felt lost.

The first time I experienced something that lit me up was in the summer before senior year of high school, when I did a program designed to expose us to the issues facing cities, partly through working with local nonprofit organizations. This was when I first connected with my peers who wanted to make a difference, even if we didn’t exactly know how. It was an eye-opening experience to break out of my cushy suburban world and see what was really happening in neighboring Boston, what dynamics were at play, and who was working to help.

This was an important clue, and gave me concrete examples of what meaningful work – for me – could look like.

In college, I majored in history because that was the subject that attracted enough of my interest to focus on it for several years and a 50-page thesis (on Victorian British and Irish history – very practical for job prospects!). But the biggest investment of my time really went into the community I had joined – whether volunteering on Saturday mornings or working in an elementary school in the adjacent neighborhood on the South Side of Chicago; conducting campus tours and helping prospective students to find out if our school was a good fit; being a resident assistant in a dorm; or serving on and then co-leading the student-run crisis hotline.

Another clue: I gravitated much more toward doing rather than academics.

Nearing graduation, I briefly tried to land a lucrative consulting job (until I bombed that interview – and also realized the only part of that work I wanted to do was the pro bono piece), and then tried to get a nonprofit gig, only to strike out by the time I graduated. I went back home for the summer confused about my direction, and locked into a lease that I had to find a way to pay for.

Some people have the benefit of knowing early on what they love to do, and what they are great at. But I think the vast majority of us panicked inside when we got the inevitable question, “what do you want to be when you grow up?” – and maybe we responded with a quick answer, or something that made the adult asking smile.

As we get further into our careers, we’re supposed to be grown up – to already be settled on our career path. We have responsibilities. We have expectations to uphold.

But what if, underneath all of that, we’re still wondering, or wishing, what else is out there?

person on a bridge near a lake
Photo by Simon Migaj on

What if we could ask questions that invite possibility of something better, something that would make that younger version of ourselves proud: What makes you light up? What brings you joy? How can you bring your experience into a new realm? How can you do work where your expertise is truly valued?

These are the questions that light me up…because I know how they’ve unlocked the clues that have brought me to the work I get to do every day.