Learn, Earn, Discern — A framework for weighing job roles

David Doherty
7 min readApr 24, 2022

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Over the years, I’ve developed this framework which I’ve found useful for considering jobs across industries as well as having a concrete verbiage with existing and potential hiring managers. Obviously it’s catchier if it rhymes so I called it Learn, Earn, Discern (L.E.D).

When you’re in your early 20s you may prioritize earnings — perhaps to pay off your student loans; or prioritize learning as you may feel you are entering a profession where there is a lot of based knowledge required to be successful. If you’re later in your career and feeling stagnated you may prioritize title over money as a way to enter a new band of seniority. If you go to the job market, try to have a clear picture of what your goal is, to avoid accidentally taking a role that sounded good but doesn’t meet you larger goals.

A visual is below:

A high-level framework

Learn

What are you going to learn in this role?

And importantly, are these skills you want or think will help you in the future. With your first job out of office you may have 2 opportunities where you learn an equal amount, but one job will teach you COBOL, and another language will teach you Rust. You may be equally interested in learning both, but they have different popularity patterns.

COBOL vs Rust

The popularity may not be crazy different (vs. say Python/Java), but Rust is a hyped language and may have big growth, it is certainly talked about a lot by lots of CTO-type people I speak to. COBOL on the other hand might earn you lots of contract work as the average age of a developer in COBOL is 55+ and it is entrenched in some industries. So have a think about what skills you’ll learn and how you can leverage them in the future.

Programming languages is one skill, but there are many others: algorithms, tools, concepts, development methodologies, and so forth. Build yourself a radar of things you want to learn and focus in on those areas. Additionally, be aware of the quality of your learning. A big tech firm may be known for specific technologies or practices: Meta built React so being there would likely give you more rapid learning than at a place that has just adopted it. Netflix is known for A/B testing its code releases.

Asides from ‘hard’ technical skills don’t forget about people management skills or organizational processes. Firms may have their own values and principles on software development.

There is also domain knowledge to learn. A high frequency trading firm may teach you a lot about market structure and financial products; whereas a health diagnostics startup may teach you about biology. For many it is hard to commit to an industry, so if you want to remain untethered to specific industries also consider how much of a prospective role may have you focused on industry specific issues vs. building technical knowledge.

Zooming back out, ideally the skills you learn will be durable for as long as possible to maximize its utility throughout your career!

Earn

What are you going to make in this role?

The earn portion of the framework focuses on remuneration which generally adds up to hard currency, but perhaps at different points in time.

  • Cash
  • Cash Bonus
  • Public equity
  • Private equity
  • Durability of earnings

Cash is the simplest and is generally in the employment contract and paid at a predictable cadence.

Cash bonuses can vary. Some firms may have very concrete % of total comp, paid at specific points in time. Others may have highly variable comp based on your management’s perception of your performance. Mileage will vary.

At some traditional financial firms, total cash compensation will have a ceiling, with anything above the ceiling being paid out in RSUs (restricted stock units), potentially with clawback provisions. Most developers won’t have to deal with this, but management may. The rationale was that the GFC (great financial crisis) exposed abhorrent risk-taking and regulators pushed for this compensation style. Less regulated firms (e.g. hedge funds) are more likely to be able to pay in all cash.

Technology firms are much more likely to use equity as a key part of total compensation. Listed technology firms (GOOGL, FB, etc) use RSUs as a stand-in for cash. They typically vest on a quarterly schedule and you can sell them immediately if you so wish. That gives them a more ‘cash-like’ feel, though you need to factor in a few potential complications:

  • Are those firms printing new shares to give to new employees (i.e. diluting the value of the firm)?
  • Is the firm profitable, and therefore the value of the shares are more likely to be stable?

Private firms, such as early stage start-ups are generally going to offer you options rather than RSUs. If you get in early enough your strike price is going to be very low, and the potential appreciation in the stock will be very high, and the tax liability may come in the form of long-term capital gains (which is currently lower than income taxes). However, you have to factor in the risk/reward with a healthy amount of optimism. There are many more complications:

  • Will the company have a favorable liquidation event (generally an IPO)?
  • Will there be much dilution of your share value between now and then?
  • Are you comfortable paying money out of your pocket to exercise (i.e. buy) the shares in a company that is still private?
  • If you leave the company, will you be forced to exercise the shares, and if you can’t afford it, or are worried about it; are you okay walking away from the potential upside of those shares?

This is all just context to consider. Three companies may offer you packages that they claim to be equivalent, but there are no hard and fast rules to compare and contrast. Finally, how durable is the company’s financial situation; obviously they need to be around to pay you!

Discern

How will your experiences carry over outside of your organization?

This last part of the framework relates to discernible skills. Some are more recognizable to other employers/investors than others. For example, if you learn Rust in one job, that is a recognized programming language that other employers may have a need for in the future. However, if you learn an employer’s custom programming language, you’ll have to figure out how to let others know what was relevant about it to their needs.

Title is one that is often lauded, though mapping titles between employers can also be challenging:

  • CTO at a 5 person startup != CTO of Google
  • Director at bank A != Director at asset manager B
  • and so forth

Financial firms are very confusing, Managing Director at one firm can be the equivalent of Partner at another. VP may have two different meanings within the same firm (as per a previous employer). Within management, HR groups tend to know the structure of different firms, and will use things like team size, budget size, and so forth to try to level. Technology firms tend to copy each other, though as they get bigger the ‘importance’ of each can vary wildly.

The last part is potential brand recognition. If you’re going to be a developer advocate, a contributor to a public good, or expected to be the external face for the company; then you also have the ability to sow seeds for future career opportunities. Hopefully you’ll have opportunities wherever you go, but having a natural ability to network with new people can open you up to unexpected opportunities down the line.

Overall

The reason I drew the original visual as a triangle is let you think about how you would slice that triangle up. If you speak to an employer and bombard them with all your thoughts across that whole spectrum, you will appear to be inconsistent or unclear as to what you want. So prioritize your needs!

Prioritizing money

It’s tempting to just prioritize money, naturally. But if you’re one year out of college that might mean making an extra $5k. That’s a terrible way to start your career as you may find yourself unable to leapfrog from there as your friends with slower starts take on big interesting roles with fat paychecks.

Early in your career you should prioritize learning, and bet on skills that will become very relevant for your career plans, or if you don’t have career plans — skills that will make you very marketable. If you’re unsure of what your goals are picking a brand name employer will be a surprising tailwind. Weirdly people place great emphasis on “Oh, they were at Goldman’s”, and “Oh, they were early at Google”.

I’ve rarely seen anyone prioritize the last piece of the puzzle when assessing opportunities, as it’s much more abstract. You can picture yourself being happy learning a lot; or by earning a lot. But beyond the initial frill of ‘Oh, I’m a VP|IC5|etc’, title tends not to make you happy on rainy/hard days as much as the other 2.

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David Doherty
David Doherty

Written by David Doherty

I write about Fintech, it's past & future, leveraging 20+ years of experience in leadership roles at large Fintechs

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