I had a recent emotions & finance conversation with a man—let’s call him Abdullah—who was laid off. Abdullah described sending out 200 job applications over ~6 months and getting one interview (and ultimately no offer). He described himself as feeling “dejected,” “demoralized” and “in despair.”

His question to me: “How do I stay motivated?”

The Dark Side of Freedom

This article isn’t about how to persevere in the face of repeated setbacks. It’s about how to cope with freedom when we aren’t used to being free.

Many high-performing high school students struggle to adjust to college (like me). Not only is the stage much bigger, with many more unfamiliar faces, a higher level of competition and more difficult material, but we suddenly transition to an environment where there is much less structure, fewer guardrails, and almost total autonomy. Some people figure out how to become self-starters pretty fast. By contrast, I was on academic probation my sophomore year.

(Ironically, I’m now a professor at the same institution that put me on academic probation. If you ever needed proof that where you start isn’t where you’ll finish, this is it.)

Transitioning from W-2 life[1] to self-employment (or unemployment) is like the transition from high school to college, but with even fewer guardrails and less structure. In a salaried job, there is a regular structure that someone gives you—be at the office at 9am, and leave after 5pm, on these days—as well as a job description that tells you what to do: write this report, call this customer, load this box into this truck. If you do something wrong, someone will tell you. If you do enough things wrong enough times, you will be punished in a very tangible way.

None of this exists for the self-employed or unemployed person. There are no set work hours, no weekends, and it’s not even clear what you are supposed to be doing. If you are doing things wrong, nobody is there to provide you with feedback on what you’re doing wrong. At least in college, there’s an academic adviser who tells you to pick a major, what classes to take, etc. Once you sign up for a class, the professor tells you when and where to show up, what to read, etc., and if you do a bad job, you at least get feedback in the form of a grade. When Abdullah sends in a job application, the company won’t even tell him that he got an F. Just radio silence.

My point to Abdullah was that when we live in a structured environment for a long time—like high school or a W-2 salaried job—we get used to the structure and lack of freedom. When we suddenly (sometimes involuntarily) transition to a less structured or totally unstructured environment like college or unemployment, our brains are just not used to the freedom and don’t know what to do. Creating our own structure and discipline is something we have to systematically learn how to do and get better at. Abdullah described wasting 50% of his time on Reddit and Instagram. In the past 3 years that I’ve called myself an entrepreneur, I’ve wasted at least 30% of my time. But that was probably closer to 70% three years ago, and something like 10% today. It’s 10:49 AM right now and I have been working for the last three hours—and on stuff that I don’t even get paid for!

The Insecure Overachiever

Abdullah and I had one thing in common in terms of background—we both worked for one of the “MBB” consulting firms: McKinsey, Bain and BCG. These three companies have similar cultures and recruit similar people.

McKinsey was very explicit in the type of person they sought to hire: the “insecure overachiever.” The profile is a person that is very strong academically, with many resume-type achievements, and is still insecure about their status and place in the world and as a result needs external validation. As I’ve done my own internal emotional exploration, I understand the psyche of this person (me) much better.

To me, the insecurity of this person is essentially about a very fragile sense of self-worth. The Insecure Overachiever’s self-worth rests on external achievements, usually of an academic or professional nature. Most of you are Insecure Overachievers (I see the email addresses of my subscriber base). Importantly, the Insecure Overachiever doesn’t have pillars of self-worth other than external achievement—think of a stool with one leg. You knock out that leg, and the stool falls over.

The dominant emotion for the Insecure Overachiever is fear. Fear of not getting the “A,” fear of not having the top performance review, fear of not being accepted into the prestigious school or hired by the reputable firm. The narrative inside this person’s head is:

-          If I don’t get an A, I’m a bad person

-          If I’m not the top performer, I’m a bad person

-          If I don’t get into school X, I’m a bad person

-          If I don’t get the job at Y, I’m a bad person

Fear is a very powerful motivator! I have a lawyer friend who said that everything he’s achieved academically or professionally has been because of his own fear, of what would happen if he didn’t achieve.

This is the same fear that motivates people to work hard at consulting firms or high-pressure startups. I liken the fear to a slavemaster with a whip. In a structured environment like Abdullah’s last company, that motivator is very clear—Abdullah can see the slavemaster, and feel the lash of the whip, every day that he goes into the office.

But what happens when Abdullah is set free, there is no slavemaster, and no whip to drive him forward?

Motivation without the Whip

I don’t know exactly what motivation without the whip is called, but I know it’s real. I know it’s real because it’s what has me writing this note at 11:21 AM without any promise of reward or punishment.  The only “whip” here is the whip I hold to myself, which is that I promised that I would publish an emotions and finance note every Friday, come hell or high water.

Psychologists might call this “intrinsic motivation.” I don’t know, maybe. For me, there are a number of emotions that now guide the work that I do, all more prevalent than fear:

-          Pride (I love telling people about my emotions & finance project)

-          Excitement (I can’t wait for the semester to start—I can’t imagine anything more fun than forcing a bunch of undergraduates to listen to my rants about the valuation of the stock market)

-          Anger (I’ve learned to appreciate the feeling of being pissed off that something is broken, and fixing it)

-          Anxiety & overwhelm (I get a chance to reinforce the identity that I’m someone who does what I have to do even when I don’t feel like doing it. I always feel better afterwards. This is the idea of becoming a machine who just puts in the work, no matter what, because it’s a habit)

I told Abdullah that although his fear would be a great motivator for him in fits and starts, if he wants to do more enduring work in the world, he needs to start listening for these other emotions as well. What’s he proud to show people? What’s he excited to work on, even without promise of punishment or reward? What does he see in the world that immediately makes him angry? How can he embrace his fear, and act from the place of the fear in a way that helps him reinforce the new identity he wants to create for himself?

For you, the Insecure Overachiever, this is about keeping the "overachievement" but dropping the "insecurity." Trust me, you will feel a lot better when you figure it out.

Exercise

Journal on the following or discuss with a friend.

1)      Noticing

In what areas of my life or work do I lack motivation?

Where does fear motivate me, i.e., if I don’t do X, some bad thing Y will happen to me?

How does the label “Insecure Overachiever” sit with me?

2)      Further noticing

In what areas of my life or work do I feel pride, excitement or anger?

3)      Action

The action is about practicing tapping into pride, excitement or anger, which are all power sources separate from fear. Adopt the mindset of being a scientist, experimenting with different methods to access your own internal power.

What action can I take that gives me a chance to feel pride, in relation to work? E.g., if you take pride in your photography, the action might be to share one photograph you’re proud of on social media.

What action can I take that gives me a chance to feel excitement, in relation to work?

What environment can I put myself in temporarily, or what is a conversation I can have, that gives me a chance to connect to the anger I feel about what is wrong with the world?

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[1] For international readers: the Form W-2 is a document your employer provides to you at the end of the year detailing your salary and related benefits. You use it to prepare your annual U.S. tax return. “W-2 person” is slang that refers to someone that has a normal job with a regular salary, as opposed to a self-employed person whose income is typically highly variable.