The Unicorn's Guide To Career Pivots

Don't just follow a Career Formula, figure out how to become a Unicorn instead

“This Biglaw job is terrible,” I once complained to a friend. “The work actually really sucks and I have zero autonomy. Maybe I made a mistake going into law.” My friend, who was a few years ahead of me in another demanding industry, gave me some perspective.

“You know, it’s like this for all of these prestigious jobs,” he said. “It’s the price you pay for this kind of career. You just have to suck it up until things get better.”

At the time it sounded like good advice to me. Be patient, and wait until you get promoted to better work. But as time went by I realized that things never *actually* got better. And it wasn’t just me. It seemed like all of us who went into high paying prestigious careers—whether it was in law, finance, or something else—were absolutely miserable. We were all Careerists who were running on the same terrible treadmill for years, dreaming about a day that things would get better.

For me, that day never came. Six years into my legal career, I decided to leave the law, and joined a legal tech startup as an entry sales rep. My experience there helped me helped me reflect upon why my previously high paying prestigious career made me so unhappy.

The problem was that I was trying to follow a Career Formula

Just like everyone else. Careerists all try to engineer professional success by following the same exact plan. So everyone ends up in the same highly competitive environments where everyone fights for the most interesting work. And since there’s so little to go around, the vast majority of Careerists end up spending their days doing the most mind-numbing, commoditized work.

In Part 1 of this article, I will try to break down why most people who follow Career Formulas end up miserable. And in Part 2, I’ll try to provide some guidance on how to become a Unicorn—someone who does meaningful work that pays well.

Part 1: Why Career Formulas Make You Miserable

A. Career Formulas lead to fierce competition

Why do so many smart, ambitious people have such strikingly similar career goals? Maybe it’s pressure from parents or teachers early on in life. Or maybe it’s trying to gain validation from society. I don’t know, exactly. Whatever it is, all the smart & driven students end up becoming Careerists who follow what I call a “Career Formula”—a structured path from school to work that’s supposed to end up with you in a highly compensated senior role in law, medicine, technology, finance, etc.

The problem with following a Career Formula is that you’re basically choosing to compete against Careerists who are just as smart & driven as you.

The lawyers know exactly what I’m talking about

When you decide to take the LSAT, you’re deciding to compete against a subset of driven college students who want to go to law school. Then, if you end up at a good law school, you’re surrounded by driven law students who all got a similarly high score as you. And when you do well in law school, you’ll likely end up at a firm where everyone is just as smart & driven as you.

The Careerist competition never ends, whether it’s trying to make partner, landing major clients, or achieving career milestones. As I wrote in It’s All Supply And Demand:

Years later you’ll find that credentials can really only get you through the front door. Once you get in, the game continues. Your peers are just as smart and hard working as you, plus they have the same qualifications. For example, once you get into a top firm, you won’t make partner unless you beat out your peers—all of whom jumped through the same hoops to get to where you are. The better you do, the harder the game gets.

B. Growth opportunities are rare

Part of why it gets harder as you move up is because there are so few growth opportunities. When you go after the same goals as everyone else, you’ll likely be targeting Established Firms that have very few interesting assignments to go around. As a result, it’s incredibly hard to find assignments that help you develop the skills you need to take your career to the next level.

Why are there so few growth opportunities?

It’s because Established Firms typically operate in mature markets. Take Biglaw for example. I’m going to generalize a bit here, but they typically focus on a few different practice areas where there’s steady demand, because that enables them to generate steady profits, forecast revenue, and hire accordingly. They can’t bet big on new, unproven markets because it would come at the expense of existing, lucrative revenue streams. It’s too big of a risk.

In mature markets, all firms have a mix of (1) a tiny bit of interesting work and (2) a ton of grunt work. The interesting work is hoarded by the most senior, experienced practitioners. Occasionally they’ll let up-and-coming mid-career work “above their pay grade” but for the most part, the interesting work is kept by those who are experienced. I mean, that’s what the clients want too. If they’re paying exorbitant fees to Established Firms, they’re going to want the most senior people working on their matters.

This pattern extends beyond the legal industry. For example, in technology sales, the biggest, most lucrative deals (“enterprise sales”) are handled by the most senior, experienced account executives. Having a junior account executive run enterprise sales is too risky for the company. The odds that the junior rep messes things up is way too high. It doesn’t matter how brilliant of a salesperson that junior rep is—they won’t get the opportunity.¹

I witnessed this same exact thing back when I was a Biglaw junior associate. A senior associate I was friendly with once told me about how her days filled with grunt work like managing doc review and preparing deposition outlines for her seniors. I was shocked. She’d graduated at the top of her class, from a top ranked school, and was absolutely brilliant. I couldn’t understand why they didn’t let her do any of the interesting work.

“I’m okay with it though,” she said. “The job pays so well that I’ll ride this out for a few years, and then go somewhere else where they’ll let me do more substantive work.”

C. Everyone has to do shitwork. Right?

I’ve written extensively before on the concept of shitwork. It’s basically the type of uninspiring work that leads you to hate your job. As I wrote in Profitable Misery:

The biggest surprise to me as a young associate was how much time I spent doing tedious, annoying tasks, like reviewing documents, checking for typos, or building chronologies. I’ll call it sh*twork. I get why sh*twork needs to be done but it’s not why I went to law school. What I didn’t understand then, that I do now, is that there’s virtually unlimited demand for sh*twork.

Every legal matter only has a limited amount of “real work” that needs to be done by a lawyer. Like prepare witnesses for depositions, come up with arguments for your case, or actually going to trial. So the demand for “real work” is quite limited. Especially compared to sh*twork.

Many years after I left Biglaw, I began to figure out why my senior associate friend never got the chance to do interesting work, like running depositions, speaking at hearings, or going to trial. There was just too little interesting work to go around. On the flip side, there was an unending amount of Shitwork involved in litigation—like managing doc review and preparing deposition outlines. The rare interesting assignment always went to a select few others who knew how to play “the game” ie. corporate politics.

Do you enjoy playing politics at work?

To be clear, I’m agnostic about corporate politics as a concept. I mean, personally I hate it, but at the same time, I understand why it exists. Politics is just a reality of working in an established organization. And you know what? Some of you will actually thrive in that game. If that’s you—stop reading! Keep following your Career Formula and keep working for Establishment Firms because you have an unfair advantage in that world.

But if you’re like me and want to minimize politics, working for an Establishment Firm will be an unending struggle. Getting promotions and gold stars will be challenging because no amount of hard work and intelligence will let you move forward as quickly as your politically savvy peers. If you’re ok with the tradeoff of working at an Establishment Firm—playing a game where you don’t have advantages, but always having a big paycheck working at a high status employer—then you should stay on that path.²

If not, you’ve got to completely let go of the Career Formula you’ve been following, and do something different.

OK, so what should I do instead?

This is where most people get stuck. They know they need to pivot to something different, but aren’t sure what. Truth is, it’s because they’re still stuck in the old way of thinking—that they need to find some other Career Formula to follow. They’re trying to imagine some existing job opening that would be perfect for them.

Unfortunately, that perfect job opening doesn’t exist. Because the best jobs out there are designed for specific individuals. They are designed *for* you. Employers recruit these “Unicorns” and then structure the organization around them. These jobs are more than just jobs—they’re a set of responsibilities that are tailored to your unique strengths and weaknesses.³

How do I become a Unicorn?

Unfortunately, there aren’t any Career Formulas to become a Unicorn. That’s kind of what makes them so rare. If anyone could just follow a pre-set formula, then everyone would do it, and Unicorns would be everywhere. So you won’t find a step by step guide to becoming a Unicorn.

However, there are some common patterns or themes. I’ve gotten to know quite a few Unicorns, and noticed that they all ended up where they are in large part due a few different factors that catapulted them forward. In this next section, I’ll break down some of the patterns and themes I’ve noticed.

Part 2: Common themes among Unicorns

A. They choose work they’d enjoy doing forever

To become a Unicorn, you have to first select work that you genuinely enjoy. That’s because one of the most important factors for becoming a unicorn is how many years you spend engrossed in the work. Whatever work you choose, you have to do it for a really long time for all of it to compound. It’s not just skills—it’s also your network and judgment. You can’t just force yourself to do work that you don’t enjoy. Because you’ll burn out, quit, or pivot after just a few years.

This is the complete opposite of what Careerists tend to do

Careerists choose work based on what they’re told to do. So they end up following the exact same path as other Careerists. They all pile into the same jobs—in law, medicine, venture capital, finance, tech, or whatever—that likely offer jobs that don’t fit with their personalities. Is it a surprise that Careerists often wake up one day and suddenly realize that they hate their jobs?

They never chose the work they wanted to do. Instead they just tried to change themselves to fit into a career path that others succeeded in. Had these Careerists chosen work they were *meant* to do, they’d be a lot happier in the long run—which means they could’ve compounded their skills, network, and judgment over many years.

Choosing the right kind of work for you

So when deciding the type of work you want to do, you should absolutely pay attention to what you enjoy. Childhood hobbies, or things you do in your free time offer hints to what that is, exactly. As you try to figure out what you’re meant to do, keep the following considerations in mind:

• First, the work must be useful in a business context. If what you enjoy most is, say, watching TV or bowling, or something along those lines, you need to choose something else. The good news is, there’s likely a LOT of other things you enjoy doing that can actually be useful in a business context. Keep an open mind and think broadly—there’s gotta be something on your list of enjoyable activities that fits the bill.

• Second, try to understand *why* you enjoy doing that type of work. The underlying reason matters more than what the work is. For example, if you’ve decided that you truly enjoy telling stories, think about why. Don’t just default to the idea of becoming a full-time writer, for example. Instead, try to understand why you enjoy telling stories. Maybe you realize that you like creating new worlds and constructing narratives. Which means you can potentially work in a wide range of roles, like creative marketing or designing video games. Choosing the right entry point is super important, so best not to limit yourself to a single industry. Think more broadly.⁴

It’s so important to pick something that you truly enjoy, for the right reasons, because effectively what you’re doing is making a long term bet. You’re betting that in a decade or two, you’ll still enjoy what you’re doing. This is SUPER important because that’s an absolutely necessary component of becoming a Unicorn. It takes time for others to recognize your talent. Once they do, that’s when they start creating roles designed specifically for you.

B. They keep an open mind about where they work

When first making your pivot, it’s important to avoid having any preconceived idea of what job you should take. Remember: Your ultimate goal is to end up at a job that’s designed specifically for you. One common mistake I see people make when pivoting is that they fall in love with a very specific job posting. Don’t do this!

There’s no such thing as the perfect job opening

Every single job posting out there is designed for some imaginary “perfect” employee. Employers fill them with an unending list of requirements and nice to haves, knowing that the person they eventually hire likely won’t meet all of them. If you’ve ever written a job description you know exactly what I mean.

So what should you do instead? Well, you’re not going to get recruited for a Unicorn job right away. In the meantime, you need to find some kind of steppingstone job that helps you develop skills and make contacts. So for that first jump, keep an open mind about where you’ll work. Some considerations as you decide:

• Choose a different kind of organization than what you’ve worked at previously. If you didn’t fit in at your previous job, it’s very possible that it wasn’t the right size. The very thing that makes you feel like a fish out of water at a big company might be what makes you a perfect fit for a small business. Or vice versa. For example, after years of struggling in big orgs, I realized that I belonged at a startup. Which was validated after working at a startup. Everyone there kept complaining about the constant change or being an underdog—all of which didn’t bother me at all. In fact, I found them energizing. That was a clear sign I was at a place I belonged.

• Go where you have unfair advantages. Find a place where your background—whether it’s your personality, work experience, or whatever—lets you ramp up more quickly than your peers. For example, for experienced lawyers who are looking to pivot to something else, choosing to join a legal-adjacent industry (like joining a legal vendor or recruiting firm) can give you a big leg up because it leverages your experience and contacts. This is exactly what I did when I pivoted from being a litigator to joining an e-discovery tech company.

• At the same time, don’t be limited by your past. You don’t necessarily have to pivot right away to something related to your previous work experience. For example, a few years ago a lawyer friend of mine wanted to make a pivot to tech sales. At the time there weren’t any good job openings at legal tech companies. So my friend decided to instead join a startup in a completely unrelated space—cybersecurity. After building up sales skills for a few years in that space, he later easily transitioned into a great legal tech role. By then he had both sales and legal experience, which made him an easy hire for the tech company he ended up joining.

In the end you have to play the cards you are dealt, and make the best decision at that exact point in time. When you decide to make your pivot, you won’t know what jobs will be available. So keep an open mind, and take jobs that help you move closer to your ultimate Unicorn role.

C. They embrace the idea of being different

It’s going to be super tempting to see what other Unicorns have done successfully and map out a similar career path. My advice: Don’t. Unicorns found opportunities that fit into their unique personalities, that made sense to them at that particular point in time. If you try to emulate their path, you’ll be disappointed. Because you’ve got a different set of strengths and weaknesses, and are facing a completely different economy.

I’ve made this mistake before

Early on, during my pivot to legal tech, I made this exact same mistake. Around three years in, I decided to become a VP of Sales (VPS). Lots of people in the startup community who I admired happened to catch their big break by first becoming a VPS. It was an enticing role. They paid far more cash & equity than the sales rep jobs I was qualified for at the time. It seemed like a good goal to shoot for.

The problem was, it wasn’t a good fit for me. My substantial legal background gave me zero advantages on the VPS track. To the CEOs and board members, I looked like every other overly ambitious junior sales rep looking to get into management. Why would they bring me on as a VPS when they could hire someone else with decades of management experience? You didn’t need an understanding of the legal industry to do well in that role, because the job was less about selling and more about building an organization, forecasting revenue, and managing people.

The timing was bad too. Those who I admired got their big promotion to VPS while they worked at hyper-growth companies that had a huge need for sales managers in their organizations. Promotions came relatively easy to them. The startups I worked for, on the other hand, did not grow as fast and accordingly there was very little demand for sales managers. There just wasn’t enough of a business need to promote me.

What I decided to do instead

It took me a while to accept, but eventually I realized that forcing myself to become a VP of Sales was too much of an uphill climb. I mean, would I even like the job? I loved selling, not reviewing other people’s deals and dealing with personnel issues. So instead of trying to win the VPS game, I decided to play a completely different game. I decided to continue succeeding as a sales rep, but in my own, different way. As I wrote in The Slow Track To Success:

In 2019 I decided to step off the management track to become a pure individual contributor. I stopped caring about whether I’d ever find an establishment job, or an executive role. It was perfectly aligned with who I was authentically. An underdog with a smartphone in hand, who could make things happen just by figuring some shit out.

Figuring what out, exactly? Well, social selling. As I described in Go Where You’re A Unicorn:

[O]ne of the earliest things I learned how to do was to leverage social media for sales. Cold calling law firm lawyers was super ineffective, but all the execs told us to do it because it was part of an existing playbook. I did the cold calls and emails like I was told to— just to keep the higher ups happy. But in my free time I would start posting on LinkedIn, and it eventually helped drive inbound leads.

In this game I had a huge unfair advantage. Lots of them, in fact. For example, I knew what type of content resonated with lawyers. I already had connections in the legal industry who would interact with my posts. And any time something wasn’t working, I could just send a group text to my old law school friends to ask them for their feedback and advice.

Going off the beaten path

Also, at the time, no one else in the legal tech space was doing anything remotely similar to what I was doing. I mean, some people in other industries were kind of doing it. But social selling wasn’t a thing yet, at least not like it is today.

That experience led me to realize that I shouldn’t try to find a new Career Formula to follow. Instead, I should try to be different. Instead of following a career path, I thought about the challenges I faced day to day, and tried to apply creative solutions to solve them. I didn’t realize it then, but I was starting to develop judgment. Judgment about what types of content could help drive sales in the legal industry. Judgment that very few people had. That, plus my skills, contacts, and reputation, ultimately led me to be recruited for a Unicorn job myself.⁵

D. They position themselves in front of emerging trends

The final piece of the puzzle is to always make sure you’re working at the edge of one or more emerging trends. Right now the biggest one seems to be generative AI. As I wrote recently in The Lawyers Are Leaning Into AI, I believe generative AI is the most transformative technology that we’ve seen in the legal industry in along time.

But the emerging trend you position yourself in front of doesn’t have to be technology. For example, one major trend has to do with how work has become decentralized via the “gig economy.” In the legal industry, that’s led to some interesting implications.

For example, for many years, the only way a corporate client could receive legal services was through Biglaw firms. But with the “gig economy” all that’s changed. Today you have outsourced providers, flexible talent platforms, and labor marketplaces that let legal professionals bring their expertise directly to clients. Not to mention small firms. A large bureaucratic “middle-man” organization like Biglaw is no longer the only way. Experienced practitioners serve corporate clients without this middle-man, and with minimal overhead, can provide value at a much lower cost.

Another example: The growing influence of social media on the business world. I’m not talking about Youtube influencers. I’m talking about professional networking or generating clients through LinkedIn. Years ago, you’d have to go to happy hour or fly to a conference to meet a few contacts. Today, you can meet a ton of people in a very short amount of time, just by leaving a comment or two every day. The Internet has democratized access to VIPs and potential clients in an unprecedented way. And this trend is accelerating.⁶

These are just some of the trends I’ve noticed. There are many others, and if you’re a subscriber, you know that it’s something I frequently write about. The point is, when you decide to pivot to work you enjoy, try to do ride an emerging trend that’s moving fast. That way, there’s plenty of opportunities to go around, and they can’t be hoarded by a people with experience. Find a niche where you can become a true expert, and dominate the space.

When money is an obstacle

Ok this article is way longer than I expected. But before I wrap up, I want to address the elephant in the room: Money. Over the years, many people have told me that they can’t pivot because they can’t afford to take a pay cut. It could be student loans, but it could also be a mortgage or family obligations. If that’s you—take heart. To start your journey to becoming a Unicorn, you don’t have to switch jobs right away.

Instead you can remain at your job and continue to collect a steady paycheck. Focus on figuring out what kind of work you enjoy doing, getting an understanding of where you might want to go eventually. Some examples of lawyers who kept their day jobs before making a big pivot:

• A Biglaw associate who tries to stay ahead of the curve by joining the firm’s technology committee to learn about new technology and how buying decisions are made;

• A law firm partner who builds a LinkedIn following to help with recruiting associates and generating new clients for the firm; and

• A general counsel who launches a niche community to connect, network, and understand best practices for legal departments.

In each of these examples, the lawyer in question ended up spending years at their day job while building something separate on the side. Eventually when the time was right, they can make the jump. And by the time they do that, there will be minimal financial risk.

So you don’t have to quit your job right away. Remember: Everything I wrote in this article involves themes and patterns. It’s not a step-by-step guide. You should move at your own pace, and design it around the rest of your life—not the other way around.⁷

Conclusion

At the end of the day, life is too short not to do work you love. If you find a job you truly enjoy, and find that you can do it forever, there’s a good chance you can end up becoming a Unicorn. Not only is it a lot of fun, it’s also incredibly lucrative. And you don’t have to quit your day job right away. So if you’re struggling at your job, wondering if there’s something better out there, I hope this article makes you reconsider what you’re doing with your career. I hope that it helps you start charting a path to something better.

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1. Juniors do on occasion get to work on interesting assignments “above their pay grade” at Establishment Firms. But it requires some combination of (1) being good at corporate politics to get a sponsor who funnels that work to you; (2) attrition at the higher levels that forces the organization to give you interesting work; or (3) quitting and lateraling to another Establishment Firm to a more senior position with promises of getting better assignments (ie. politics). So it can happen.

2. This is especially true if you’ve already been identified as one of The Chosen Ones. As I wrote in Climbing The Corporate Ladder:

Becoming one of The Chosen Ones means you’ve been selected by a sponsor—a powerful mentor who puts their credibility at risk to support you. Sponsors do things like place you on strategic matters that help you develop valuable expertise that the firm needs. They protect you. You’ll get opportunities to get in front of clients, and receive intel about the market. You’ll get visibility, so people will know your name.

3. I’m using the words “job” and “employer” but the real way to think about work is to view yourself as a partner. So yes, jobs may come in the form of a full time W2 role, but it may also come as an advisory relationship, joint venture, etc.

4. When I first pivoted to legal tech I was tempted to find something in legal research because I’d clerked and was good at reading and interpreting caselaw. However, my big insight was that the work I could do forever was sales, because I enjoyed persuading people. That’s why I went to law school—I wanted to become a trial lawyer. If I worked in a legal research startup as my first legal tech role, I might end up doing more reading & analysis type of work, which would take me farther away from the whole point of my pivot. That’s why I went to the relatively unglamorous e-discovery technology world. So focus on the work, and why you like the work—it may take you down a road you didn’t imagine going down—but it’s the right path.

For more on my pivot to legal tech sales, check out How I Found My First Legal Tech Job

5. Arnold Schwarzenegger’s career is one of the best examples of how being authentic to yourself can lead to massive opportunities. As I wrote in Embrace What Makes You Different:

You could imagine an alternative world where he tried to blend in. Maybe he would’ve stopped working out so he could slim down and look like one of those “small and skinny” leading men in Hollywood during the 1970s. Maybe he would’ve declined any opportunities related to bodybuilding to avoid being typecast into narrow roles. In that world, he never would’ve agreed to the Whitney museum exhibit or the leading role in Pumping Iron.

Once Schwarzenegger made a name for himself, and became a proven A list star, everything changed. Directors would mold characters to fit his personality. For example, they would add humor—one of Schwarzenegger’s strengths—into the script. Opportunities to take on unexpected roles came up too, like when Ivan Reitman invited him to play the leading role in Twins, a buddy comedy film that crushed it at the box office and proved that Schwarzenegger could be more than just an action star.

6. This trend has led me to write extensively on how to use LinkedIn to find clients and generate revenue. If you’re interested in this topic, sign up for a paid subscription to my newsletter where you can access articles like The Right Way To Do LinkedIn and Optimizing Your LinkedIn Profile Page For Marketing.

7. Having said all that, don’t underestimate the economic value of becoming a Unicorn. I’ve been mostly writing about individual careers here, but sometimes entire firms can be Unicorns. The classic law firm example is Wachtell. A big part of the reason why they generate so much revenue is because they’re a Unicorn in the M&A market, and it’s a huge part of their brand. As I wrote in Sell Outcomes, Not Hours:

Could Wachtell generate more revenue by doing lots of other types of work? Sure. Maybe the firm could roll out an expansion plan, opening offices throughout the U.S. and internationally. It certainly has the ability to recruit aggressively from other firms and pay handsomely to lure laterals away.

But doing that would destroy the firm’s brand. It would likely dilute its focus, and over time, Wachtell would lose its mystique. Maybe it would be forced to adjust its hiring standards, and give in to client pushback on fees—especially on relatively routine matters. Then, when the occasional $44 billion case comes along, Wachtell would not be able to command the fees that it otherwise would.