Keeping Options Open Is Closing Doors For Students

Growing up in Toronto in the 80s, there weren’t many birthday party options for those of us born in the dead of winter. As it was too cold to do anything outside, bowling alleys were pretty much the only game in town. But there was one notable exception. The Mad Hatter’s Tea Party was a venue where, as one contemporary recalled, “every weekend, a new group of unsuspecting middle-class Toronto parents would drop off their seven to 12-year-olds for an hour or two of birthday revelry, replete with bodily endangerment, ritual humiliation, and untold health-code violations.”

Parents weren’t allowed on site, so kids were picked up in a “limo” (i.e., converted hearse) and carted to the strip mall storefront. The party was downstairs in a creepy bunker-like basement. First, lights were turned off for a strobe light pillow fight (with, as one participant remembered, “urine-stained pillows”). Then lunch was served in the “hot dog room” where kids were encouraged to throw hot dogs and condiments at each other. All this was prelude to the Mad Hatter’s whipped cream fight: partygoers ushered into a room caked with dry, clotted white stuff, handed an oil drum of whipped cream, and instructed to have at it. After everyone was covered from head to toe came a prison-style hosing down followed by shopping cart bumper cars; the Mad Hatter had purloined a bunch of shopping carts kids would careen through a rickety plywood maze and smash into each other – often with someone inside. Before getting back in the hearse, any injuries or hurt feelings were soothed and soon forgotten with all-you-can-eat ice cream. “If you had been crying an hour earlier,” said one participant, “now you were, like, best party ever!”

Those of us who were there remember it fondly, if oddly:

The Mad Hatter was Canada’s kinder, gentler answer to Action Park, the dangerous New Jersey amusement park chronicled in the documentary Class Action Park and remembered with the same combination of nostalgia and horror. Whether biking without helmets, calling late to say you’re “staying over at a friend’s house,” or just being a free-range kid, young people used to choose to do all sorts of risky things, and parents didn’t stand in the way. For example, kids used to get married, but not so much anymore. In 1980, the median age of first marriage was 22.0 for women and 24.7 for men. It’s now 28.6 for women and 30.4 for men.

What was true of leisure and life was also true for school and work. As portrayed in Fast Times at Ridgemont High, high school students took jobs at the mall, working at Perry’s Pizza, as an usher at the movie theater, or if they were lucky, as a shift supervisor at All-American Burger. The relationship between the job and future plans was unclear and probably unconsidered. Since the heyday of Brad Hamilton and Jeff Spicoli, American teen participation in the labor market has fallen nearly in half, representing nearly 40% of the overall pre-Covid decline in workforce participation and significantly less risk-taking in aggregate.

In today’s Mad-Hatter-less, Action-Park-absent world, young Americans optimize for optionality. By delaying marriage, they’re optimizing for relationship optionality. By refraining from taking any old job, they believe they’re optimizing for career optionality. And just as kids didn’t blanche at taking a job at the mall or a restaurant, they were less hesitant to enter a trade. Schools taught woodworking and welding and it wasn’t uncommon for students to graduate from high school and pursue careers in carpentry, welding, plumbing, or as an electrician. Optimizing for optionality poses a major challenge to construction trades that operate on a general contractor – subcontractor modality with most work completed by specialized subs. So 18-year-olds who might be interested in construction have a hard time swallowing a decision to join a company that only does framing, drywall, windows, or HVAC.


The 18-year-olds who don’t pursue a trade are probably going to college. For over fifty years, college has had a symbiotic relationship with optimizing for optionality. The whole point of college fantasy viewbooks is to communicate this to prospective students: you can become whoever and whatever you want (just as long as you enroll and pay tuition and fees for at least four years). Everything is possible. Yes, you’ll have to select a major. But our programs of study take you anywhere and everywhere. And why only pick one when you can pick two; at some colleges, 40% of students are double majors. All the better to keep your options open. Moreover, as all degrees lead inexorably to good jobs, it would be foolish to pursue first jobs which reduce options; so career services complacency reigns. Optionality is the sine qua non of America’s accredited colleges and universities.

Believing you can major in one thing and make a living doing something completely different really does belong in a fantasy viewbook. It’s equivalent to Bill Gates / Mark Zuckerberg dropout logic (i.e., they dropped out and became tech billionaires, ergo dropping out is a good idea). It can happen, it’s just highly improbable. It turns out double majoring is more common for wealthy kids. Students at schools with higher percentages of Pell students or underrepresented minorities are less likely to double major. And that makes sense: wealthy kids can afford to keep their options open. As such, double majoring may be a fair metonym for the entire college option-optimizing enterprise.

Optionality continues to be a North Star for many 20- and 30-somethings. According to a recent survey of 7,000 Gen Z workers, 70% believe they can make a career out of freelancing. And one in four dream of a career as a social media influencer where each TikTok video can lead to a different, exciting career. But optimizing for optionality is beginning to become problematic for the real jobs on offer, which are increasingly digital. Up until a few years ago, software developer was the paradigmatic digital job. You could graduate as a computer science major or attend a coding bootcamp and have a reasonable (but by no means guaranteed) shot at an entry-level developer job. None of this felt like closing off options, in part because software developers could conceivably develop anything. While developer jobs remain plentiful (although less so at tech giants and venture-backed companies that have enacted attention-grabbing cuts in the past year), the talent shortage has already metastasized to a thousand different combinations of business knowledge and specific platform skills (and not only because software development is on the verge of being automated anyway). So now it’s Salesforce, ServiceNow, or Databricks skills layered atop industry or functional experience e.g., Workday experience in a hospital setting. And as generative AI is applied across industries and business functions, entry-level positions (i.e., not requiring relevant experience) may become an oxymoron, like we’ve seen in cybersecurity. And that spells trouble for job seekers who’ve been chillin’, optimizing for optionality.

A few weeks ago, I spoke with the founder of a company that implements, configures, and integrates warehouse management software. The talent shortage he described sounded familiar, perhaps because to a 22-year-old, warehouse management software sounds nearly as option-foreclosing and unappealing as welding; few willingly opt for such a level of specialization at a young age. According to the warehouse management software CEO, “they all want to be strategy consultants.”

I know something about strategy consultants because my first job out of college was at McKinsey. I worked on four different problems across four different industries; I was jack of all trades, master of none. Perhaps the most important thing I learned is that people who remain strategy consultants for more than a few years become pretty much unqualified to do anything except consulting (maybe business development on a good day). At some point, you need to choose what you want to be when you grow up and take some risks; there are diminishing returns to keeping your options open. There may even be a Laffer curve for optimizing optionality (beyond a certain point, options decrease).


Gen Z is willing to work hard but wants options. Unless it’s possible to turn back the clock on risk-taking, we’re not going to realign labor supply and demand and close the skills gap without building new pathways which sugarcoat specialization by actively marketing optionality to job seekers. Helios, a Workday advisory partner – helping clients maximize their investment in Workday – has launched Rise, a pathway to hire, train, and deploy hundreds of new Workday associates. While Workday would appear to be as option-foreclosing as warehouse management software, Helios goes out of its way to educate prospective applicants on the fact that Workday is now the people operating system for more than half the Fortune 500, and that, as a result, if you’re interested in people (i.e., psychology majors, sociology majors, other non-STEM people people), the Workday ecosystem is a perfect place to launch a career. Moreover, Rise is a “program,” trained apprentices become “consultants,” and the salary trajectory along the pathway is clear and compelling.

The same thing is possible across a thousand skill gap sectors, even construction. Forge is a venture-backed intermediary “rebuilding the trades from the ground up.” Forge’s 12-week apprenticeship program trains on a wide range of construction skills. Like Rise, Forge highlights its pathway’s benefits and builds in options. Both Rise and Forge recognize that in order to attract top Gen Z talent, they need to borrow some of the optionality that’s been key to college’s remarkable run.

State governors are all about pathways to good jobs; in a survey of 2023 state-of-the-state speeches, the National Governors Association identified pathways as the top postsecondary education theme. But governors should recognize that new pathways are less likely to scale unless they can convince applicants they open more doors than they close. And also that few companies are likely to do this work on their own (because it’s easier to leave positions unfilled than make the necessary investments). Most new attractive, option-stuffed pathways will be built by intermediaries like Helios and Forge – in the business of hiring, training, and deploying scarce talent – or intermediaries like workforce boards, unions, nonprofits, and community colleges receiving public subsidies to do so. Kudos to Governor Gavin Newsom and California for recognizing this by recently allocating $175M to intermediaries via apprenticeship innovation funding.


Kids today aren’t allowed to play, they’re not allowed to do anything... It’s like… the only acceptable things for them to do is sit like marshmallows in front of their videogame... and that’s safe.
- Harry Stinson, former owner of the Mad Hatter

There are obviously good things about optimizing for optionality. For example, we know college graduates who are forced to take the first job that comes their way in order to make student loan payments are more likely to be underemployed (although this hasn’t been an issue for three years due to the continuing Covid “emergency”). But it’s undeniable that young people used to take more career risks. And that’s not only a problem for employers, but job seekers themselves. Because any higher education observer who’s not as mad as a hatter now realizes that nothing closes off more options than excessive student loan debt. In an irony only an indebted, underemployed college graduate can truly appreciate, by optimizing for optionality and delaying choosing, college has become the riskiest thing.