Three Things to Look For in a New Job

How to know a career choice is right for you.

Ask yourself these questions individually – in absence of one another.  When you think about one, don’t worry how it impacts the other two.

It happens to almost all of us.  And it happens when you least expect it.  It happened to me on a Saturday morning in a forest.

I was exhausted from working six 100-hour weeks in a row.  We had just submitted a $720M proposal to the US Army for a major communications program.  Four of us had sat in a conference room writing one of the largest proposals in our lives.  We worked with more than 100 other individuals to gather the costs, technical designs, schedules, and write-ups that we would ultimately cram into the proposal. 

It was a world-class proposal, and we eventually won the program.  But just after submitting the proposal, something strange happened to me.  I felt a wave of complete disinterest and apathy wash over me.  This was the pinnacle moment in my career, and I could not care less.

Maybe it was temporary burnout from a really taxing two months, but I never did recover the enthusiasm I once had for my work.

After sleeping for two days, I went on a mountain bike ride.  This was my solace from all of the technology, relationships, stress and pressure of work.  I always wind up zoning out when I’m riding – focusing only on keeping those two wheels on the tiny, rutty, single-track dirt trail in the Chicopee Woods forest. 

My mind started wandering to thoughts and ideas I hadn’t had in more than a decade.  I started thinking about what my life would have been like if I had chosen to follow a different career path.

And then it happened.  I realized that, while I was very good at my job, I had no love for it.

I spent a lot of time over the next two years thinking about what I really wanted to do with my life.  I knew that there were a few things I really wanted out of my career, but I had to balance those with the needs of my family. 

Being the engineer that I am, I wanted to try and create an equation that would let me identify the variables and assign weights to the things that mattered most.  I tinkered with this “work happiness” equation a lot.  What I eventually figured out was there were only three metrics that really mattered to me.

Once I understood these metrics, I have successfully applied them to every job and project I’ve undertaken since.  Each time I’ve created roles and opportunities that refilled my passion and enthusiasm in ways I couldn’t have hoped for before. 

The Three Questions

I constantly ask myself of every opportunity and career decision these three questions:

These questions seem pretty straight-forward and I’m sure most of you ask yourself these questions too. 

But there’s a real trick here. 

You have to ask these questions IN ABSENCE OF ONE ANOTHER.  In other words, when thinking about what you love to do, you need to think about it without thinking about how it changes the world or how much money you can make doing it.

Will You Love What You Do

It’s hard to do something you don’t enjoy doing.  That’s work.  But when you absolutely love what you’re doing, it’s no longer work. 

Absent of the other two metrics, this would be best defined as ‘play’.  Think about it.  What would you do if money was no object and you could be selfish about what you spend your time on?  For me the answer is very simple with a number of options. Make beautiful things.  Travel the world.  Drink good rum.  Spend time with inspiring, enthusiastic, collaborative people.    

What is your favorite thing to do?  Go fishing?  Hugging puppies?  Doodling?  Write down that list of things you would do if money was no object and it didn’t matter what impact it had on the rest of the world.

Will You Change the World

This has to do with whether or not your life’s work has meaning.  Some of the most enjoyable things I’ve done in my life are things that had a major impact on others. 

When I was a medic, I enjoyed the fact that my work helped heal others.  I remember tending to a man that had just been in a car accident in front of me on the highway.  I bandaged him up and stabilized him until the ambulance arrived.  I felt an amazing sense of pride that I could help this person in his most critical time of need.

I also enjoy teaching others.  Not necessarily in the classroom sense, but more about things to which they’ve not yet been exposed.  I loved having teenagers come through my old company to get a tour of what it was like to work in a creative startup environment.  Watching them think about ideas that they have and realizing that they could actually make those ideas become reality gave me a sense of fulfillment.

Building products and technologies that benefit countless others truly brings me joy.  To watch someone look at something I helped create and realize just how valuable this thing would be to them…that’s a special moment.

Life is fleeting and short, and our time working is even shorter.  Think about things that you can do that make the world a better place.  In absence of the other two metrics, great examples of careers that change the world are humanitarian aid, construction, experimental science, medicine, working with recovering addicts and suicide prevention.

Can You Make Life-Altering Money

Work, at it’s core definition, is trading your time in one skill to acquire the time or products of other skills.  In early human history, a hunter would trade animals he caught for firewood to keep warm at night.  Or farming vegetables and trading those for protection from other tribes. 

We’re really not all that different,  except we use a placeholder for that traded value – money.  You work.  You get a paycheck.  You use that paycheck to pay for the basics of life – housing, food, medicine, etc. – and for recreational activities and products. 

Making life-altering money, to me at least, means making enough money to cover the essentials for the rest of my life, and allowing me to work in careers that make less money but increase the value of my other two metrics.  In other words, if I’m “set for life” I can think about free philanthropic work without worrying about making the mortgage payment. 

To a point, money can’t buy you happiness, but it can afford you the ability to seek happiness without worrying about your cost of living. 

The key here is to look at opportunities that are lucrative or have a tremendous financial upside. 

Putting It All Together

I like to use this chart to examine how new opportunities impact my three metrics.  Some opportunities max out on one axis, while others barely make it down the line. 

In my situation out there on the mountain bike, I knew that I could make good money (but not life-altering money).  I also knew that my love of my work was waning and falling fast.  And I knew that my work, while impactful to a few, really wasn’t going to make a huge impact on the lives of most of the people in the world.  On this chart, I was pretty close to zero on all three axes.

Write down a list of job opportunities that appeal to you for each category.  Remember to focus solely on each aspect one at a time.  When thinking about happiness, don’t think about money or how it changes the world.  Think about what you would be good at doing that you would love to do.

Maximizing All Three

This chart is a little bit deceptive, because it suggests that you really can maximize only one or two of these categories at a time.  The biggest life hack I can teach is to look at this chart in three dimensions instead of two.

When you do this, you’re looking for career opportunities that wind up in the upper corner of your ‘cube’.  You’re looking for ways to combine aspects of items in each category into a single career choice.  I’ll bet that you’ll be surprised by what you find if you go through this exercise.


Think about this chart in three dimensions instead of two.

Let me know what you come up with as your dream career opportunity, or how your current job ranks on this chart. The career paths best suited for each of us are commonly far different than the path we’ve taken. 

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