How To Do Work You Love

An interview with Jeff Hittner, founder of Your Project X.

When we are young, we often have dreams to do something special with our lives. As we grow older, society’s expectations set in and push us toward a fairly standard path that looks more or less like this:

School — College — Job—Graduate School — Another, More Stressful Job — Retirement (if you’re lucky)
Image Source: http://imgur.com/AoyJaas

As we move further down this path, pressures mount and fewer opportunities for self-discovery and exploration present themselves. We get a stable job, a mortgage on a house, and a loan on a car, but at the expense of pursuing more fulfilling careers.

Indeed, the latest Gallup State of the American Workplace report finds that two out of three workers in the US report feeling disengaged at their current workplace. We are burned out, over-worked, and unhappy, because we work for a paycheck.

Yet, our best work comes out when we are aligned with our purpose.

To make a massive shift toward prioritizing well-being over well-earning, it is our social imperative to figure out how to help more people design work that would make them happy.

Image courtesy of Unsplash

I sat down with Jeff Hittner, founder of Your Project X, a social venture that helps people build careers they’ll love. Read on to learn what he had to say about fulfillment at work and how to start building a life — and a career — you’ll love.


What led you to launch Your Project X?

It really stems from that oh so horrible question I was first asked when I was ten:

What do you want to be when you grow up?

I have searched. I’ve worked in consulting, started an internet company, been a teacher and a professor. I moved to Belgium to get my masters in Cultures and Development Studies. I moved to Granada, Spain to learn Spanish and teach English.

But as soon as I completed each stop, the same question reemerged: what do I want to do with my life?

And each time I asked myself I felt stumped, scared and frustrated.

That’s when I finally recognized a pattern… If I kept trying to answer the “what” question, I’d forever feel overwhelmed and uncertain. Instead, I needed to make the choice about who I wanted to be in the world, connecting all my decisions to that choice. It has kept me grounded ever since.

Lots of people are unhappy at work. What do you think is causing this ‘epidemic’ of dissatisfaction?

There is a complete disconnect between how we ready people for the world of work and the reality they run smack into when they enter it. We’re taught — at school and from family — that we can enter into a job and have an immediate impact.

The reality is far from this. We run into major resistance and quickly feel powerless. For those who are further removed from school, the encroachment of work into all hours of our day plays a major role: email 24/7, calls from home, weekend assignments. It feels like a burden when we’d rather be doing anything else.

If a person is feeling that something is missing in their career, what should they do to start making a tangible change?

First, they should realize they are not alone. When I gather folks together to tackle the possibility of changing careers, many discover this for the first time. They had been stuck inside their heads feeling like they were “the crazy ones” listening to that little voice telling them to take the road less traveled. In our programs, they quickly realize that they are not crazy and they are not alone. The sense of relief that comes from this is a powerful catalyst for change.

Second, they should understand that we all need support to make change. We need a community to hold us accountable to making small steps in new directions.

Many young people today want to go into startups and are interested in entrepreneurship. What advice would you give to someone who has an exciting idea but is not sure where to start?

Don’t get sucked into the myth that if your idea is great the business should take off quickly and magically. Starting a business is a series of small experiments — in our programs we call them Trojan Mouses because from the outside they make look like small failures, but to the thoughtful entrepreneur they are micro-experiments. Success comes from testing and prodding the opportunities around you and moving forward when the perimeter fence you’re evaluating comes back with a “safe to enter” response.

At young age, we often have dreams and aspirations that get buried under the ‘adult’ obligations as we grow older. How would someone start finding their way back toward a more authentic self?

In our programs we approach this a couple of different ways.

The first way is to acknowledge the expectations you are burdening yourself with. I recently ran a workshop with MIT Sloan MBA students and like everyone else, they were struggling with unrealistic expectations — expectations of status (to reach a certain job type and title), of success (how quickly they should “achieve”), of focus (because you’re paying $100k for graduate school, you should “know” what you want to do).

Once we unpack these expectations, we start to move towards a more authentic self by changing the lens and focusing on activities that unveil what makes us feel alive.

One fun way to do this is to take an afternoon and go on a mini-retreat. Leave all that technology at home. Take yourself somewhere where you can more deeply connect with a wider perspective — go on a hike, walk through the woods, let yourself wander. Let your curiosities overtake you. See where they lead. Getting rid of distractions is key to quieting all the other voices.

How should someone balance pursuing their passions with having a (very real) need to support and provide for themselves and their family?

We tend to approach this two ways.

First, we need to make a plan. Understanding what you definitively need to keep your family comfortable is critical information.

Second, we challenge people to rethink their definition of success and financial security. If you have a partner, there should be many conversations around success. You’ll be surprised by how many people have come back to me and said their spouse doesn’t care if they make half as much if it means they carry a smile around the house.

What is one thing a reader of this interview can do right now to get on a path toward a more fulfilling career?

Email 3 friends. Ask them to describe a moment in your life when they witnessed you as your best self. This could be a moment when you were incredibly happy, a moment when those around you felt touched by your presence, a moment when they witnessed your greatest energy.

Insights like these — from the outside in — play a huge role in breaking through the repetitive thinking we often find going on in our own heads. These are the breadcrumbs to start us down a new path.


Your Project X is a social venture with a vision to reimagine the world of work. We run 10 week part-time programs designed to help people align with their purpose, enter new career fields, start a business, make an impact in their communities, and experiment their way into building the life they want. Your Project X currently offers programs in New York City and Boston.