Job searching as a generalist in the age of COVID

💌 The Roundup // 014

New York Times

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I recently concluded an epic job search. I say epic because it turns out that attempting anything consequential in the age of COVID comes with dramatic plot twists.

Friends who were kind enough to act as my sounding board over the past few months have suggested I publish some of my learnings. Given the number of people who have recently been induced into job searches of their own, I've decided to share these learnings in hopes that they might benefit those who are figuring out what's next (of course feel free to forward this along to friends you think might benefit as well).

If you can't take the suspense and just want to know what I'm doing next, skip down to the "What's Next?" section of this essay.

Finding Focus

I've spent the majority of my career as a generalist working with early-stage startups. As someone who craves variety, I've always resisted job descriptions and thrived when I can spend my time in different functions. While being a generalist has kept me engaged at work, it posed a couple of distinct challenges during my job search:

  1. An abundance of options to choose from

  2. Not being ideally suited to any of them

Early on, it felt like I would leave every coffee meeting wanting something different. I'd chat with a founder and come away wanting to start a cash-flow business or meet an investor and convince myself I should join a venture firm. When friends would ask what I wanted to do, I would provide hazy answers so as not to limit my options.

The problem is if you can't tell people specifics about what you want it's hard for them to help you. They may know someone who's looking for a director of partnerships, but if you don't express a strong interest in that role, they won't think to recommend you. Because I couldn't decide which function I wanted to target, I decided to nail down other parts of my career goal first.


At Tradecraft we used a Customer/Problem/Solution framework to help our students decide what kind of companies to apply to. It was designed to help career transitioners differentiate themselves in a sea of entry-level talent. The idea being, instead of labeling yourself as another junior product designer, it's better to be a junior product designer who cares deeply about solving marketing problems for small business owners. Since I couldn't pick a function, I needed to get clear about what kind of company I wanted to join, so I turned the framework on myself. Here's how I thought about each factor:

  • Problem was the easiest. Part of what I loved about Tradecraft was giving people access to the knowledge, network, and opportunities they needed to make meaningful changes in their professional lives. Since these problems tend to be solved by companies in the education and human spaces, I didn't need to do much searching.

  • Customer was a bit more challenging. I like helping individuals, but mostly within the context of work. I fundamentally believe that work is the ideal enabling environment for learning and that learning is what makes life meaningful. That led me to strongly consider both B2B and B2C companies.

  • Solution was one factor I knew I wanted to change. Because Tradecraft is a service business it always felt hard to get the leverage I wanted. And though I loved sharing an office with students, after 4.5 years I was ready for a change. I set my focus on a business whose core value delivery mechanism was enabled by software.

I also had to decide what size of company I wanted to join. My desire to get more leverage led friends to suggest that I consider joining a growth-stage company with more resources to turn ideas into reality. Since I tend to like the type of problems that emerge in large systems of people, a bigger company felt like the right path. However, just because I was excited about joining a later stage company didn't mean a later-stage company wanted what I was offering.

Return of the ambiguity-loving generalists

Transitioning from an early-stage company to a later-stage one isn't straightforward. Early-stage startups often hire scrappy generalists who thrive on ambiguity. After all, until a company finds product/market fit, it doesn't make sense to hire people who are too attached to specific job descriptions. But, once a company learns what works, it needs to hire people who are world-class at filling the responsibilities of particular functions. Those are rarely the same employees who helped the company achieve its initial success. More often than not, those early employees get leveled by specialists who have enough experience to professionalize each function of the business. This makes it hard to transition from an early-stage to a growth-stage company (particularly if you can't settle on a functional specialty).

What job-seekers tend to forget is that successful companies usually need to find product-market fit more than once. Companies that are good at serving customers often get requests to build solutions to help their customers meet other needs. Fulfilling these needs often requires the type of ambiguity-loving generalists who initially helped the company find initial product-market fit. The challenge is that most of the generalists who got the company from zero to one are long gone. While some late-stage employees will raise their hands to explore new opportunities, it's risky to abandon a job you're good at for something that may not work out. As I learned more about this challenge that many growth-stage companies face, I recognized it as a problem that I was well-positioned to help solve.

Just-in-time research

That insight was what I needed to start unlocking interesting conversations. When people asked me what I wanted to do next, I would say something like: "I'm looking to contribute to a growth-stage company in the talent development space that's exploring new markets or building out new offerings." That was usually enough for friends to come up with ideas for interesting people I should meet.

To prepare for meetings with founders, I would typically spend time researching the problems their company solved and try coming up with interesting ideas for how they could expand their offering. This served as both a great way to get smart on new spaces and to evaluate companies.

Because founders tend to be generalists, they were usually more forgiving about my lack of dedication to a specific function. That said, when I did see a role on a careers page that looked interesting I'd spend a few hours researching it to ensure I could talk the talk.

Since generalist roles don't often get assignments, I would try to demonstrate value by following up on conversations with some kind of asset (document, spreadsheet, slide deck) that fleshed out some of the expansion opportunities that I'd discussed with the founder.

This strategy led to lots of great conversations and a bunch of promising opportunities... which promptly evaporated once COVID-19 became a reality.

The Big Chill

On March 9th, my pipeline froze. Follow-ups never got scheduled. Emails were never answered. Startups that were thinking about expansion one week before were now desperate to conserve cash to prepare for winter (I think the timing had something to do with Sequoia's Black Swan memo). In this new reality, I realized that my positioning as a generalist who could help a company unlock its next phase of growth no longer made sense. I thought I would have to rethink my entire job-search strategy. Fortunately, not every opportunity evaporated.

What's Next?

At the beginning of February, I had breakfast with my friend Rachel. Though I've been friends with her and her co-founder Britt for a long time, and their Denver-based company Guild is one of the most successful startups in the human capital space, I had never really entertained the idea of working there due to my stalwart dedication to living in San Francisco. But that morning, Rachel hinted that, in the coming months, working at Guild from SF might be an option. The more I looked into the company, the more excited I got about the opportunity. The company fit with a lot of the criteria that I cared about, including:

  • Not needing to compromise between doing well and doing good

  • The chance to serve both businesses and consumers

  • A successful first product and the desire to explore new offerings

  • Employing lots of kind and smart people who I could learn from

  • Founders who I respect and admire both as people and leaders

What pushed me over the edge was something Paul Freedman shared during my final-round interview about why he was excited for his San Francisco-based company, Entangled to merge with Guild. While I can't remember the exact quote, he said something like: "Facebook won because they aggregated the most talented people they could find and aligned on the same mission. One reason that there hasn't been a truly iconic company built in education yet is that the talent is fragmented across so many different ventures. We want to come together to finally build that iconic company." 

I joined Guild at the beginning of April to lead product marketing for the company's newest offering, Next Chapter. Driven by the needs of a growing population of unemployed frontline workers, and the efforts of amazing teammates from Guild and Entangled, we were able to launch in a month. While the launch has made for an intense onboarding experience, it's also felt great to preserve the excitement that drew me to startups in the first place.

I feel lucky to have landed in such a great spot, particularly given the challenging economic climate. I also feel fortunate to have the opportunity to apply what I learned at Tradecraft to one of the most serious human capital crises this country has ever seen.

To those of you who provided advice and introductions along the way, I am truly grateful for the help you provided.


What about if you're job searching right now? Given the economic times we live in, you'll need to find your own strategy that fits.

  • If you're a job-seeking generalist, rely on your network and find ways to define your specialty (or, if you're less stubborn than me, just pick the function that seems most interesting). Also, find ways to demonstrate your value during the interview process by going above and beyond to deliver a work sample, even if you're not asked.

  • If you're a specialist looking for work, set your sights on companies that are growing quickly due to the pandemic. Don't be afraid to take a step down in terms of seniority. It tends to be a better career move, in the long run, to be underrated and move up quickly rather than to jump into a role that's a big stretch.

  • If you're just starting your career, I recommend picking a specific in-demand function (like engineering or sales) and working for companies that can provide a high enough rate of learning and brand halo to give you lots of optionality in the future. 

  • If you're going through a career transition, there may not be a lot of companies that can afford to pay you the salary you want. That said, there are plenty of companies that need help from inexpensive contractors. As you build up your portfolio of work, set your prices low and gain the experience so that once the labor market recovers you can command the prices you want.

  • To those of you who are thinking about starting something, this is a great time to experiment. Try to avoid focusing on the same problems as everyone else. Yes, remote work tools for knowledge workers could be improved, but so could financial protections for low-wage workers who've been laid-off. Poke your head outside of your usual bubble to see what kinds of new challenges the world needs you to solve.

And, as always, if I can help, don't hesitate to reach out.

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👉 The One-Touch Guide to Doing a Weekly Review: How I Go From Chaos to Clarity in 30 Minutes

(20-minute read by Tiago Forte)

Before I started working from home, I was pretty good at staying organized. But over these past few months, I've noticed myself slipping back into old habits and getting overwhelmed by digital clutter. This article by Tiago was the refresher course I needed to restore some sanity to my work routines. He shares how he conducts weekly reviews to get his inbox, calendar, and task list aligned. If you're in need of some help getting your productivity back on track I highly recommend it.

🏝 The Future of Remote Work is Not That Remote

(13-minute read by Byrne Hobart)

There's a narrative going around that the COVID-induced shift to working from home is going to cause the majority companies to permanently embrace remote work pulling the center of gravity away from major cities to places where cost of living is cheaper. While I believe we will hear lots of stories about this happening, I think this trend is overblown.

Yes, many companies will allow employees to work from home. Also, a certain group of people who have been wanting to buy houses will leave San Francisco and New York for areas with a lower cost of living. But will ambitious young people stop moving to cities to jump-start their careers? The nature of competitive dynamics and potential for lower rent prices says that more, not less, young people will choose to move to major cities after graduation.

While companies may find they are just as productive collaborating remotely, it doesn't mean their employees will achieve the same amount of career mobility in Chattanooga, TN as in the Bay Area. Despite the progress of technology, relationship building is still much easier to do in person than over Zoom. And while the internet has somewhat democratized access to opportunity, career mobility still depends a lot on who you know. Byrne Hobart points out that the same dynamics exist for startups:

There’s one important reason for small companies to locate in the Bay Area: meetings. In-person meetings are higher-bandwidth than remote meetings, although it’s unclear why. Maybe posture and fidgeting are subconsciously informative, maybe there’s a subtle Uncanny Valley effect, maybe handshakes and fistbumps transmit otherwise-secret information. Nobody knows for sure. (I don’t doubt that there are studies, but I do doubt that they replicate.)

There’s a correlation between how important someone is and how hard it is to get a meeting. So there’s a certain set of important meetings that, if they happen, have to happen right then. If the company you’re trying to partner with suddenly has a free half-hour on their schedule, do you really want to be a flight away? You could, of course, live somewhere else and fly in once a week for meetings; the market-clearing price of SF real estate has been partly determined by the cost of round trips from there to Vegas. But the missing meetings are essential.

The idea that ambitious young people will give up the face-to-face relationship-building offered by cities for lower cost of living reminds me of the argument that many B2B founders used to make that they could effectively close enterprise deals without a traditional salesforce. Even if they had better products, most found themselves losing out on deals when going up against competitors who were willing to leverage the power of interpersonal sales. Those who want to compete to accomplish big things will move to whatever environment gives them the most leverage to shape the future. For now, major cities will continue to be their best option.

🏗 Schumpeter's Gale

(16-minute read by Packy McCormick)

It should go without saying– layoffs affect workers very differently. A frontline worker who gets laid-off from a low-wage job may find it hard to pay rent, while a wealthy knowledge worker can use a layoff as an opportunity for soul searching. That said, some subset of those who've been laid off are about to get an opportunity to put their talents to much better use.

A decade from now, I predict the business press will feature stories of founders who used this moment as a catalyst to build some truly impactful organizations. Why is this moment special? Many golden handcuffs have been broken at just the moment when we are being faced with the inadequacy of our existing institutions. Meanwhile, those with influence are using their platforms to inspire people with narratives to dream bigger and build. While I worry about the destruction this moment is wreaking on many people, I can't help but still be optimistic about the creation it may inspire.

🔮 Pandemic Uncovers the Limitations of Superforecasting

(14-minute read by Jeremiah)

One of the stranger purchases that I made in 2020 was a second freezer. It currently sits humming away in our spare bedroom, stocked with meat. I remember when we bought it from Best Buy two months ago feeling worried about what we would do if our food supply chain collapsed.

But what if nothing happens? Should I feel ashamed about spending money on a second freezer? After all, it would be easy to interpret the purchase as a prediction that a food shortage is coming. If that shortage doesn't happen shouldn't I feel embarrassed about being such a crappy forecaster?

But, the truth is I am a crappy forecaster. I'm not smart enough to predict what COVID's impact our supply chain will be. That's why it's more important to optimize my decision-making for downside tail risk than the most likely outcome.

Imagine that I’m one of these crazy people you’re always hearing about. I’m so crazy I don’t even get invited on TV. Because all I can talk about is the imminent nuclear war. As a consequence of these beliefs I’ve moved to a remote place and built a fallout shelter and stocked it with a bunch of food. Every year I confidently predict a nuclear war and every year people point me out as someone who makes outlandish predictions to get attention, because year after year I’m wrong. Until one year, I’m not. Just like with the financial crisis, it doesn’t matter how many times I was the crazy guy with a bunker in Wyoming, and everyone else was the sane defender of the status quo, because from the perspective of consequences they got all the consequences of being wrong despite years and years of being right, and I got all the benefits of being right despite years and years of being wrong.

The reason it's worth buying a second freezer isn't that your analysis tells you a food shortage is coming. It's worth buying because the consequences of being unprepared are terrible, and because you, like the rest of us, are bad at predicting the future.

🌻 Redefining Hope

(6-minute watch by Jordan Hall and John Vervaeke)

Most of us have an aversion to rosy predictions during dark times. While this can be seen as a cognitive bias, it is likely a feature rather than a bug.

To survive challenging circumstances, our ancestors had to rely on the expertise of others to stay safe. Those who took advice from doomsayers rarely died from exhibiting too much caution, while those who followed the advice of pollyannas often lost the chance to pass on their genes.

But orienting yourself toward positivity isn't necessarily naive. Hope can be a rational choice. To paraphrase how Jordan Hall and John Vervaeke recast hope:

Being hopeful means maintaining an accurate view of reality while choosing to orient yourself toward the best possible outcome in an effort to increase its chances of coming to fruition.

Good advice for anyone going through dark times.



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*Header Image Credit: Evan M. Cohen