Leverage-able Experience

How can you accomplish more in your career in a shorter period of time? The answer is leverage.

May 20, 2021 | 5 minute read

When you sign on to a new job, the employer is taking a risk on you and you are taking a risk on the employer. The employer is betting that you’ll be able to fulfill the functions of the role and you are betting that the company will be an interesting place to work that provides stable compensation for the future.

Where there is perfect symmetry between the risk you and the employer are taking, your chances of getting the job are high. When the symmetry is misaligned in some way, the odds shift in or out of your favor. This is why start ups provide equity: to make up for the risk you are taking on by working for them. It’s also why jobs have requirements like a certain number of years of experience. They’re assuming someone with a certain number of years of experience is more likely to fulfill the role they need (i.e. is less risky).

On some level, your career goal is to work up the ladder as quickly as possible, which requires convincing employers to take a risk on you. Your ideal is to create a favorable asymmetric risk. You accomplish this with leverage-able experience.

What Makes Experience Leverage-able?

If the standard metric of comparison is years of experience, then leverage-able jobs will give you more value per year of experience.

Leverage-able experience is ultimately experience that is compressed and/or high-value. It’s finding a job where you’ll learn and accomplish more in two years than you would in another.

Typically, that means you have a lot of individual responsibility and freedom in your role. It may also mean that the stakes are high for what you do. Again, because the experience is compressed, you’ll typically do more in two years in a leverage-able job than in another. So you’ll have to deal with doing more in the same period of time.

You may also be delaying gratification by taking a more leverage-able role, often in the form of compensation. Again, this is why start-ups provide equity. Most early stage start up jobs are very leverage-able in that you’ll be asked a lot of in a short period of time. I’ve written about this before for software engineers: my first programming job was at a startup and I wrote more code in 6 months than my peers did in at least the first year of their career. But the point of leverage is that you can apply it, in this case to accelerate your career.

What are some examples of high-leverage roles? Aside from the obvious path of joining a start up, I’ve accidentally discovered two in my own career: teaching and starting a business.


For a myriad of reasons, if you know a skill fairly well, you should consider teaching it. I’m a software engineer by training and spent four years of my career teaching others to become software engineers. First, I taught a part-time JavaScript course in the evenings for about a year, then I taught a coding bootcamp at General Assembly for almost three years.

Teaching provides a lot of first- and second-order benefits. The most notable first-order benefit is that you will have to deeply examine your skillset and knowledge base in order to teach it effectively. You’ll have to do both on your feet if you teach a live, in-person class. And nothing will deepen your knowledge of a subject like 20 beginners peppering you with questions you never thought to ask.

The second-order benefits are amazing too. Teaching a class is a form of people management: you’ll have high achievers and low performers to manage, challenge, and inspire. You’ll also encounter all the issues that come from working with people: someone will experience a loss or a bad breakup and need time off, someone will be more focused on planning their wedding, someone will say something offensive. How do you keep things moving forward while recognizing everyone is human (and doing so in a humane way)?

Teaching is also a form of product management. It’s also a form of sales. It’s a great example of experience where “the proof is in the pudding.” I don’t have a degree in Computer Science, but I’ve taught fundamental data structures and algorithms to a few hundred people. No employer since has worried about my understanding of Computer Science topics. I also now have a network of former students, most of whom I would personally enjoy working with. Last time I needed to hire engineers, I shot out a single email and had thirty promising candidates in a week.

If you can get a job teaching what you do, I highly recommend it. It’s a lot of fun, it’s really challenging, and you’ll learn a lot. In short, it is highly leverage-able.

Starting a Business

One of the many reasons that starting your own business is way less risky than most people think is that it’s highly leverage-able. That means there are two possible outcomes: your business works out and you never need a job again. Or it doesn’t work out and when you go to apply for a “normal” job, people will generally be so impressed that you ran your own business for a while that they’re likely to take a bet on you. It’s not risk free by any means. But if you do it right, the risk can be very minimal.

While starting your own business is highly leverage-able at any point in your career, it would probably have the biggest impact early on. Every college student spends their fall semester looking for summer internships. These are almost always unpaid and generally “foot in the door”-style jobs, meaning low skill and low leverage. When you go to apply for a job, you’re one of hundreds, maybe thousands, of college grads with the same two to four internships on your resume.

If instead you started a business - literally, any business - you’d have an enormously differentiated set of experience when (if) you went to apply for your first job after college. If it doesn’t work out, you’re a kid in college who tried to start their own company. Wild! What was that like? If it does work out, you don’t need a traditional job now.

Seeking Leverage

Teaching and starting a business are two experiences that I stumbled upon and realized would be highly leverage-able, but there are many more. For instance, if you can build a large audience on Twitter and/or an email newsletter, you may never be in need of work again. I worked with a software engineer who had 30,000 followers on Twitter and she would get freelance opportunities sent to her all the time. When she needed a new job, she just posted something on Twitter. It was incredible.

On some level, this is the entire goal of your career: to collect as much leverage as you can and use it to get even more leverage-able experience. Over time, you build an accelerating flywheel with each new high-leverage role or skill you take on.