Almost seven years ago, I gave a TEDx talk that would prove to be prophetic.  The focus was on trying to resolve two seemingly irreconcilable facts: that many new college graduates were unemployed and yet there were abundant job openings for college graduates with no experience.  My explanation was one of expectations: that because college students were recruited into college with promises of high future salaries, taking anything less than a high salary would mean realizing a loss.  As long as they stayed unemployed, they could continue to dream big.  The antidote, I suggested, was the centering of meaning rather than money as the reason for both work and education.  If we shifted focus to “work worth doing”, as Teddy Roosvelt put it, we could smooth the transition into the workplace.

Fast forward to now and while it is a trait that is alternatingly praised and ridiculed, Millennials and Gen Z are noted for their borderline obsession on making a meaningful impact through their work.  But while we made exactly the transition I proposed, in a rather spectacular fashion, the underlying problem remains: the current COVID-fueled unemployment crisis aside, there is a massive disjoint between the work available and the workers who could do it.  Because while I was right about centering meaning, I was also right about realizing losses.

In the original talk, I discussed how taking a job for $40K when you expected to be making $50K feels like losing $10K, even though in a rational economic sense $40K is a gain over $0.  This irrational behavior is one of the many insights of behavioral economics and explains why, for example, someone will ride a stock all the way to zero because “it might go back up” rather than taking a sensible loss and moving on; until they sell, the loss isn’t “real”.

What I missed was that the same argument can be made for meaning.  As we centered impact in the narrative of meaningful work, we created an identical problem to the unrealized salary loss in two ways.  

The first is the unrealized loss of role impact: new grads envision themselves as stepping into jobs in which they will be empowered to have immediate influence.  This has been heightened by an emphasis on entrepreneurship as a quick route to being the boss; I once asked a class of MBAs how many expected their next job to be CEO of a startup and almost all of them raised their hands (with several c-suite startup jobs under my belt, I have never once been CEO).

But of course, stepping into immediate impact is rare.  While companies are doing a better job of adopting organizational structures that create autonomy and accountability, even in the best of circumstances it takes time to develop both the skills and processes necessary to make meaningful changes.  If new grads are unprepared for that reality, they may view roles as too junior or meaningless and choose to remain unemployed even though, just as a $40K salary is better than $0K, having some impact in a workplace is better than none and the sooner you start working, the sooner you are able to increase your impact.

To some extent, however, the unrealized loss problem of role impact has always been present: it is in the nature of all of us, and especially the young, that we feel we ought to be allowed to create greater change.  It is the second shortfall, organizational impact, that has become more acute in the time since the original talk.

When I quoted “work worth doing”, I meant not only the work we do inside of companies but the meaningful impact the companies themselves have on the outside world.  But as the gap between the rich and poor in this country continues to widen, the perception of companies has become increasingly problematic.  Whether because of systemic (the implications of gig work and the utter inability of many companies to hire and retain black people at every level), executive (#MeToo and leadership abuses like those at Away), or social justice (funding hate groups, having business dealings with Trump) failings, there is almost always a reason to say that a company is less than ideal; brands are “cancelled” on a daily basis.  Being unemployed means retaining the ability to claim the moral high ground; at least you aren’t part of a system of oppression.

Entrepreneurship factors in here as well.  Many entrepreneurs think of their businesses as improvements on existing models and it is seductive to believe that we can replicate the success of others without also replicating their shortcomings (or introducing new ones of our own).  Until we express those shortcomings ourselves, they remain tantalizingly unrealized.  So rather than take a job at an existing company with flaws, we can start something flawless, even if its practical impact is near zero; 62% of people think starting your own business is a good career move, but less than a third of business started make it to the 10-year mark.

So what do we do about it, if the problem isn’t just meaning over money, but motivating people to engage in a system where participation feels like realizing a loss?  Fortunately, loss aversion is a well studied phenomenon and existing behavioral interventions hold potential to be applied here.

For example, a number of successful experiments have combated the tendency of investors to hold on to losing stocks (called the disposition effect) to avoid realizing losses.  One standout, suggested by my friend Dan Egan of Betterment, is reframing.  In stocks, we do this by noting that selling at a loss can be seen as a gain in taxes saved.  In employment, reframing salary (“Here is what you can do with $40K.”), role (“Here is what you’ll learn in this job.”), and organizational impact (“Here is who you could help at this company.”) as gains may shift the decisions you make.

Another possibility is timeboxing.  When investors are reluctant to let go of a losing stock, advisors sometimes encourage them to set a limit for how long they will hold it.  The same can be done with employment, like explicitly committing that if a $50K+ job has not materialized within three months, you’ll accept something lower.

And finally, there is the traditional investor strategy of hedging: explicitly pairing opposing strategies to protect against risk.  For every $50K job you apply for, apply for a $40K one; for each company with seemingly untainted morals, apply for one that is working to change itself.  Applying is a nice hedge because it is soft: you’re not agreeing to take the job, but rather opening up the possibility (and, once you have an offer, other psychological biases like the endowment effect will do the rest).

I still believe in work worth doing and I’m not suggesting there aren’t legitimate reasons not to apply for a particular job; I’m still angry at Toast for offering a payout to white guys while making women and POC work longer hours for less money and it is a great reason not to work for them.  But when the fear of realizing losses keeps people in a state of perpetual unemployment, unable to make the gains they so desperately want, we need more than just emphasizing the meaning of work.  Because work worth doing isn’t about working somewhere that is already perfect; it is about making things better through our work, iterating through engagement.  And engagement beats perfection every time.

Side Note: In the original talk, I ended on a Star Trek note, about how in a post-scarcity world, the human spirit still yearns toward meaning.  I think a lot about “boldly going where no one has gone before” and recently, I’m struck by how often that where is philosophical in nature.  Uncharted territory used to mean the places we literally didn’t have maps for but lately, it feels like the maps themselves are wrong because the territory is shifting beneath our feet.  We don’t yet know what an America that confronts its racist legacy looks like or what a more equitable, inclusive version of the workplace is.  But we don’t have to travel in space to find out: instead, we can travel in time, by planting our feet and swinging our fists and fighting for our future.