Everyone has defining moments in their life, and I want to share with you one of mine.

I was just about to finish up my PhD and I was looking for a job. As you know, I was in the Air Force at the time, and while you may be under the impression such decisions are entirely made for you, this is not the case. I found a position as a program manager, which entailed evaluating proposals from scientists around the world and deciding who I would give money to in support of their work.

These kinds of jobs are usually held by senior scientists, but I didn’t know that. Moreover, the program I was applying for wasn’t exactly related to the degree I was finishing. My lab mate John, a dear friend, asked a perfectly reasonable question:

Are you even remotely qualified for that job? Without pause I told him, “Of course!”

I’ll tell you why this story is relevant to career design in just a moment, but first you have to ask yourself–

What Are You Afraid Of?

One of the biggest reasons more people don’t pursue career design is fear.

It reminds me of a story I read about a guy talking to his therapist about his relationship with his girlfriend. Everything was going really well, he was happy, but he was afraid to commit. He said to his therapist: What if it doesn’t work out? And the therapist replied: What if it does?

When you try to make a big change in your life, nearly everyone asks you the first question, when you really should be focused on the second. How would your life change if your job was an integral, sustaining, and fulfilling part of your life? What if the reason it was hard to take vacations was because you didn’t want to stop working?

A book I’ll come back to many times in this post is Chris Guillebeau’s must-read The Art of Nonconformity, where he quotes Thomas Carlyle as saying

The tragedy of life is not so much what we suffer, but what we miss.

Said another way, we are far more likely to regret what we didn’t do than what we did.

How Do I Get There From Here?

Ramit Sethi recently asked his readers a simple question: how many of you make more than $100K per year? While many were enthused about their high-paying salaries, several responses went like this

I’m in a similar position where I earn a big paycheck (though not quite $100k), but have had to make some big sacrifices and compromises to get it. Ultimately, it’s not a sustainable situation, and I want to make the leap to something completely new…but that would mean taking a $25-$40k cut in annual salary based on my outreach to prospective employers. I want to take the leap, but just can’t bring myself to walk away from that much coin. Can you tell us how you broke free of the golden handcuffs and how you got your salary back up to a comfortable level?

Let me be clear: there’s nothing wrong with making money. I’m all for it. But staying in a job you dislike simply because it pays well is not a recipe for a happy life.

Which isn’t to say the choice is rare. But the focus on financial security is a red herring.

Although finances dominate the minds of people wanting to escape their jobs, I suspect the real problem is psychological. Go back and read the responses to Ramit’s question: the vast majority of people who responded said their lifestyles had changed relatively little from when they made far less money. Many are stashing away money hand over fist, because we’re all told again and again that’s what we’re supposed to do. So why, then, does a pay cut prevent so many people from leaving a lousy job?

Here are the 3 essential steps you need to make the leap (and land on your feet).

Step 1: Know yourself

Sounds easy, but it isn’t. Again, Guillebeau says

Life planning begins with an unfortunate fact: many people have no idea what they really want to do or accomplish over the course of their time on earth.  Instead of moving toward a destination, they become mired in “life avoidance” by ambling around without a clear sense of objective or purpose.

I’d go a step further and argue that this is where the drive to earn more money comes from.  Nature abhors a vacuum so society supplies the meaning of life for you. As Marcia Reynolds discusses in this post, some people follow their craving for external affirmation and mistake it for their calling.

Guillebeau suggests a number of exercises in his book to determine your life purpose, or you can do what I did and wade through Nicholas Lore’s more comprehensive book on the subject, The Pathfinder.

Step 2: Have confidence in your abilities

Once you know what you want to do with your life, you need to assess your aptitudes. Let’s go back to my story about applying for a job that on the surface I didn’t appear qualified for.

It turns out my partially related degree was, in some respects, an asset, because the job required you to field proposals on a wide range of topics. It wasn’t possible to be an expert in them all, and coming from the outside gave me a perspective (and independence) others didn’t have. You also needed to have excellent speaking skills in order to defend your program from budget cuts, a skill set I honed as a college chemistry instructor.

So before you rule out a new job, ask yourself what skill sets are really needed to accomplish it and just as important, which of those skills are typically underdeveloped in those that dominate the field. While I couldn’t go head-to-head on science depth with my colleagues, I won nearly every speaking award.

Don’t take your aptitudes on faith either. Test them. Before I decided to pursue a writing career, I started this blog to test my stamina for writing as well as the market response. Even when my blog only had 25 subscribers, I often got as many comments as blogs 10 to 100 times my size.

But beware: as Chip and Dan Heath reveal in their book Switch: How To Change Things When Change Is Hard, self-evaluation also tends to be self-serving. Back to Marcia’s calling versus craving idea, it’s a good idea to temper your assessment with independent verification.

Once you have confidence in your abilities, you’re better prepared to follow Guillebeau’s advice and “derive security from your own competence instead of an employer.”

Step 3: Have an epiphany

When I decided to make my own career leap, those who knew me well weren’t surprised. While I had been successful at my various positions, without intending to, I communicated to my friends I wasn’t completely fulfilled.  If it was so obvious to my them, why did it take so long for me to leap? I had to have an epiphany.

Normally epiphanies are the result of an unfortunate event that causes us to reevaluate our mental models of the world. In my case, I suffered two miscarriages in the space of 10 months.  My body and my emotions were wreaked. But in that space, my priorities became crystal clear–life was literally too short to waste it on a job that wasn’t exactly what I wanted. I just had to do steps 1 and 2 to figure out what that was.

The good news is that you don’t have to suffer misfortune to have an epiphany. Epiphanies come about because our life circumstances shift our perception of fear. Those who have a near death experience suddenly realize they’re afraid of not living more than they’re afraid of failing.

As Guillebeau points out, the other way to get that kind of clarity is to “decrease the fear of the desired situation.” You can do this internally, by tapping into your emotions and creating a gradual path to change that doesn’t spook that lizard part of your brain (a la the Switch book method). Or you can do it externally, by testing your future career on the side, as I did with the blog, which encourages you to build a business while still working full time.

Surrounding yourself with voices that support change is critical to success. Don’t underestimate the powerful effect of having books like Guillebeau’s to draw strength and inspiration from while you’re going through career design. Even though I had already made the hard decision to leave my job when his book came out, I continue to have smaller epiphanies while reading it even now.

Once I decided to pursue my passion, everything after that was details.  Honestly.  You do have to go through a process of worrying over the financial specifics, as I detailed in Part 2 of this series. But you’ll simply have to believe me that as your resolve to change strengthens, the details become less important, not more so. The dollar figure of “what we need” to live on goes down all the time.

Of course, I’m also pretty confident we’ll never have to test that figure out. Pursuing a fulfilling career is equivalent to Seth Godin’s idea of bringing emotion to your work. And as Guillebeau says, that can change the world–at least your own.