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How to Find Meaningful Work in the Age of Job-Hopping

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Adam “Smiley” Poswolsky is on a mission to help millennials connect with meaningful work. As a speaker, entrepreneur, and the author of The Quarter Life Breakthrough: Invent Your Own Path, Find Meaningful Work, and Build a Life That Matters, Smiley shares insights on how to navigate the changing job market to find work that’s fulfilling. In a recent conversation with Heleo’s Assistant Editor Mandy Godwin, Smiley discussed his own wandering journey, why “quit your job” is bad advice, and how to make the best of the worst job experiences.

Mandy: You have been all over the place, career-wise. How did you get to where you are right now?

Smiley: My quarter life breakthrough happened at the age of 28. I was living in Washington D.C. at the time, working for the Peace Corps. I had a job that, on paper, was perfect. I was making $70,000 a year. I had health care, benefits, job security. You literally cannot get fired working for that department. I’d go to happy hour and tell everyone my job title, tell everyone what I was doing, and they were really impressed. They’d ask for my business card. Everything was really perfect about the job except that I was miserable. It wasn’t the right fit for me.

It’s hard when you have a job that everyone else thinks is awesome or checks all the boxes. It fits salary, looks cool on LinkedIn, is prestigious. The mission of the Peace Corps is to promote world peace and friendship. That’s great. But if deep down you know it’s not the right fit, what do you do? For me it was this period of turmoil and crisis. I felt a lot of anxiety and a little depressed. I even got shingles, a nerve disease often related to stress. It’s common in people over the age of 70, not twentysomethings. It was really when I met other young people going through this exact same thing, I was able to turn this crisis into a breakthrough and find more meaningful work.

I’ve had a wandering journey. I studied film in college. I moved to New York to work in film. After that I lived in Argentina for a while. I worked on the Obama campaign in 2008 and that brought me to D.C. to do politics. I do believe if you’re wandering, you’re okay. You’re not alone.

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The truth is only 27% of college graduates in this country are working a job that’s related to their college major. Increasingly, we’re going to have people that have very diverse, eclectic careers. That old method of picking a job right out of school, staying in the same field or company for 20 or 30 years, is just dead. It’s over for a variety of reasons. It’s okay to wander if you wander with intention, and you’re treating your career like an experiment.

Mandy: How do you find that intention? What if you get into your early 20’s and you’re like, “What’s my purpose?”

“No one has one purpose. This ‘quit your job, find your calling’ is crap that’s sold to us by internet marketers.”

Smiley: First of all, no one has one purpose. This “quit your job, find your calling” is crap that’s sold to us by internet marketers. I’ve had ten purposes, at least, and I’m only 33. It’s about figuring out what you care about most now and being willing to adapt and change, and to learn by experimenting and by doing. Trying a lot of things and seeing if it’s the right fit for you.

I’m really glad I had that job at the Peace Corps because I learned that that wasn’t the right setting for me. I wouldn’t have known that if I didn’t have that experience. You don’t learn that from a website or from reading about it. You have to just go and try it. I encourage people, especially people in their early career or when switching to a new field, to gain as much experience as they can. Then reflect constantly on what it is you’re learning, what you like about your job, your boss, your work culture, the environment, the mission of the organization, and then what you don’t like.

Even if you’re in a job you don’t like, you can still learn. Make that time as intentional and strategic as possible. Say, “Hey, this is not perfect, I don’t want to do this forever, but while I’m here I want to learn this. While I’m here I want to explore this thing that’s really interesting to me.” Or I want to get guidance from this supervisor, this mentor, or focus on this skill.

Mandy: You can’t figure out what you like until you do something that you don’t like.

Smiley: Totally. A lot of people that have found meaningful work have experienced the complete opposite. They’ve gone through the dark, hated their job, hated their life, or were pretty miserable. They’ve experienced what that was like so that they can then have the breakthrough and find something better. We’re taught to find the “perfect job.” That’s not what I’m talking about. It’s not about finding perfection, it’s finding the right job for you right now.

Mandy: You talk about success being relative, that someone who’s working at Google might want to be a freelance writer, and the freelance writer might want to be working at Google. It seems as though many people think that success looks like one thing. Are you trying to break that down?

Smiley: Yeah. I’m trying to get people a little bit closer to finding what success looks like for them. I’m on Facebook, on Instagram. We’re constantly bombarded with other people’s highlight reels, victories, and achievements. We should celebrate those accomplishments, but if you’re constantly comparing yourself to others, it’s hard to find what you actually care about.

For every person I meet that works the coolest job at Airbnb, Google, the Peace Corps, or the White House, I know people in those same positions at those same companies that are miserable and want to leave. I know a lot of people that work for themselves that are entrepreneurs or artists and don’t have to go to an office, and get to work from a coffee shop or a living room in their sweatpants. Everyone is jealous of them because they post on Instagram, “Look at my life!”

They’re also miserable and they want a more stable job because it’s not working for them. The grass is always greener. What are the metrics for you to define success, happiness, fulfillment, a good use of your time? They don’t teach you that in college or graduate school. If you can develop ways of thinking about and analyzing your own journey, that’s a lot more powerful than constantly putting yourself up against everyone else.

Mandy: Do you feel it’s harder to be young these days, or at least harder to separate your idea of success from other people’s’? Because we have so much media coming at us?

Smiley: On the one hand, there’s so many opportunities available to our generation through technology and social media. We can put our ideas out there. We can raise money. You can find jobs via LinkedIn or Twitter. Those are great tools. But at the same time, with all of those options comes increased anxiety. With just my phone, I have 17 apps that are all showing me everyone’s cool lives. It’s really hard to be content. Thirty years ago, unless you picked up the phone, you didn’t know what your friends were doing on a day-to-day basis. Now you see it every second.

“No one finds career fulfillment with a click or a swipe of an app. It takes time. It takes years of getting good at something.”

Also, patience, that’s something that we’re not good at. I’ll be the first to admit that millennials don’t have a lot of patience. It’s something we need to work on, this idea that this doesn’t happen overnight. No one finds career fulfillment with a click or a swipe of an app. It takes time. It takes years of getting good at something, discovering what you care about, gaining the reputation, the career capital to make a difference and get that respect. It’s great that we’re eager and want to make a difference, but there has to be a balance and understanding that it takes a little bit of time.

We need to have a mindset that encourages, “Hey, this is going to take some time. There’s going to be obstacles and stumbles along the way.” It’s not about the press of a button. It’s not like it’s a guided vacation. It’s about that journey.

Mandy: Along those lines, do you feel like one of the biggest obstacles to millennials’ success, as some people claim, is the mindset of “someone told me that I can’t do it, therefore I can’t do it.”

Smiley: I think that millennials have a lot of enthusiasm. This generation is coming in hungry. They want to make an impact. But they don’t do well with feedback—or they do much better with positive feedback. You hear this is stereotypically the “trophy generation,” because we’re so used to saying, “Here’s a gold star! Here’s a trophy! You did good on little league!”

I think we need to do a better job with constructive feedback. If someone is saying, “Hey, next time it would be better if you did this because…” we have to be willing to be like, “Okay, cool.” And not, “Oh my God, I hate my job!” I can admit to sometimes not being great at that. We need to be able to know that someone is trying to help us learn and get better.

Mandy: It’s interesting. Adam Grant has talked about how people who are grumpy and disagreeable but are willing to give you that critical feedback are actually the people that you should have on your team, because they’re going to be the people who will help you to grow.

Smiley: We need people to give real, open constructive feedback because we’re so used to being like, “Great job, great job!” You don’t learn when someone tells you that. You don’t want someone who’s just mean, or someone who’s just always negative. But if they’re doing that with the intention of hitting targets, of making more good in the world, or having the company succeed, that’s what it’s about.

Mandy: Looking towards the future, how do you feel you’re going to implement some of the things you’ve learned in your own career? Do you think that you can use these lessons beyond the quarter point of your life?

Smiley: I think this framework applies to people of all ages. It’s not just about quarter life twentysomethings. I called it that because at the time I was going through this I was 28. I couldn’t really tell my parents’ generation what to do. I don’t know what it’s like to have a mortgage or raise a family. Hopefully I’ll write that book when I’m ready.

“Every career path and field is changing, even traditional paths like medicine and law. We need a mindset that’s much more flexible.”

In terms of career strategy, in the changing job market this applies just as much to someone who’s 52 as it does to someone who’s 22. Every career path and field is changing, even traditional paths like medicine and law. We need a mindset that’s much more flexible. Instead of thinking of this singular career ladder, where you get on at the bottom and at the age of 65 you’re like, “Whoa, I’m at the top of the ladder, I’m done!” think about your career as this extended pond of lily pads, where you can move in any direction given what makes sense for you and your purpose. The roots are all connected underneath. That’s what’s meaningful to you, what you care about. The surface might look very different—what you’re doing on a day-to-day basis.

You might be on one or two lily pads right now. You might have your foot on a full time job, but be doing a creative project that you care about on the side: a blog, learning to code, doing a women-in-tech support group. Whatever it is, you have a lot of different things happening. That’s just going to make your pond of lily pads stronger and more interesting as you go.

Mandy: That economy has been called the sharing economy and the gig economy, depending on who’s talking. It gives you some great opportunities. You get a lot of flexibility. You get to chase new dreams. But it’s also led to a lot of job insecurity. How does the future look for that?

Smiley: Currently, 53 million Americans are freelance. That’s over 30% of the American workforce. That number is expected to be 60 million in the next five to ten years. The social safety net and the systems that we have in this country from a workforce development standpoint have not caught up to the reality of how many people now work. The tax structure, health care benefits system, those need to change. Those systems need to change to make it easier for someone like me who works for themselves to get health care, to pay a reasonable tax.

You see models like the freelancer’s union, but I think in the coming years this is going to be a countrywide thing, because so many people are going to have two or three or four different jobs at the same time. Because full-time jobs are becoming outsourced or, sadly, getting replaced by automation. But maybe that’s an opportunity for us to think about living more meaningful lives.

But, if you’re going to do that we also need to talk about a universal basic income, about that safety net. It’s not fair to say just because a computer took your job you have to struggle. We have to have a system set up so that people can have the traditional things that companies have supplied even if they’re freelance.

We saw how it worked in the recession. People lost their pensions overnight. That contract was broken in 2008. I’ve got to do work I care about, make a difference, work for a company for a little bit, but then do something else. Because at the end of the day, you’re kind of on your own.

These are conversations that are starting to happen, but we’re not there yet. I’m excited about a future where work is much more meaningful, where people get to be more creative in their work, where people get to spend their days doing something they care about, and where we as a culture and society value that in a way that we haven’t before.

This conversation has been edited and condensed. 


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