When to quit your job and how to compare new opportunities

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One of the most popular emails I receive goes something along the lines of:

“Hi Rohan,

*paragraphs of context*

*paragraphs of context*

*paragraphs of context*

I don’t know what to do. Should I start looking for another job?”

I have two observations after reading these emails:

  1. This is a question that is top of mind for every recent graduate in their first job.
  2. Those paragraphs of situational context are necessary, because this is a complex decision.

The question of when to leave your first job is intimate and messy. It requires you to consider an endless number of factors, deeply understand the context of your situation, and have a level head when making the decision.

It’s why in my last article on the highs and lows of a job, I mentioned that you should not make any drastic career decisions when influenced by flavor of the week emotions.

It’s natural to think that changing jobs will solve all your problems in the workplace. But every job, even the best job in the world, is a rollercoaster of emotions.

This is a decision only you can make, and you need to be in the right mindset.

Furthermore, given the importance of each person’s unique situation and context, it’s especially difficult to write an exhaustive how-to article on this topic.

As an alternative, I structured my decision making process into four parts:

  1. Guiding principles for career transitions
  2. A simple formula to figure out when to leave
  3. Factors that you may want to consider
  4. Factors to avoid consideration

Guiding principles for career transitions

Prior to making career decisions, you should write down your guiding principles. For those of you in college, this is a great exercise to do prior to committing to a full time role. When done right, these principles will help you choose between multiple opportunities.

One way to generate ideas for your guiding principles is to ask yourself, “what are fundamental beliefs I have about my career that I want to stay true to?”  

I thought of 3 principles for myself:

Principle 1: Make career decisions with a hypothesis-driven mindset, eliminating aspects of work that I don’t enjoy and constantly seeking roles that are more fulfilling and energizing

If you’ve been reading 2 by 22 for a while, this principle should not be a surprise. My primary career philosophy is to manage my career like an experiment. I try lots of things, learn about myself, and keep pivoting to find opportunities that best fit my interests and strengths.

By not taking this approach, I’ve noticed some peers making career decisions that they end up regretting. For example, after realizing they dislike -- or even hate -- some critical aspects of their job, I’ve seen people continue to stay in their role or move to better brand name company in a similar role. This tends to happen when prioritizing compensation or prestige over self-interest.

Principle 2: Prioritize skill development over compensation because skills unlock long-term opportunity (and therefore long-term compensation)

Compensation is always important. Especially to students with debt, it can seem like the most important consideration for your next career move.

However, I view compensation as either “good enough” or “too low.” If multiple opportunities cross my threshold of “good enough,” I no longer consider compensation and focus on other attributes.

I always prioritize the skills I would build over moderate compensation differences. I believe the best route to long-term compensation and self-confidence is to focus intensely on skill development early in my career.

That being said, I acknowledge the privileged position I’m in to be able to make this trade off without pressure to pay down debt or support dependents. If you subscribe to my belief of skills over compensation, think about how much compensation you’re willing to trade off for a better skill-building opportunity.

Depending on the industry you’re entering, you may find that some opportunities are better skill-building opportunities and higher compensation -- a win-win.

Principle 3: I am responsible for managing my career. When making career decisions, prioritize myself before prioritizing the interests of my parents, manager, company, or others

Your career is exactly that -- your career. You will be in situations where your manager, parents, or peers want you to make a specific career decision. But this is your career. You are the person who’s going to spend 40+ hours per week dealing with the repercussions of this decision.

It’s always helpful to broaden your perspective and hear others out, but when it comes to making a career decision, be wary of choosing something primarily because others want you to do it.

This includes pressure from your manager or company to remain loyal and stay beyond your desire. The days of spending your entire career at one company are over. Today, professionals in many countries change companies every few years.

You should be able to maintain good relationships with your company by leaving in a professional and respectful manner.  

Making career decisions becomes a lot easier with a handful of guiding principles, because they help clarify what you are optimizing for with every tradeoff.

A formula for leaving

Here’s a formula to simplify this complex decision. You should leave your job when…

Perceived benefit of leaving  > Perceived benefit of staying + Friction of changing jobs

I use the word perceived because you will never really know what the true benefit of leaving or staying is. However, with proper diligence you can get an idea of what your future will look like in your current role or in a position at another company.

Perceived benefit of leaving

When examining a new opportunity, make sure you dig deep into the role and understand the day-to-day. One way to do this is by making a list of everything you like and dislike about your current role. Then, ask targeted questions about the new opportunity to understand how it is similar to or different from your current role.

If you have a good friend at the company, talk to them to get a realistic perspective of the company and position. This is my favorite (and most effective) tactic to learn about new opportunities.

Perceived benefit of staying

When assessing your current role, make sure you’ve been at the company long enough to really understand what sticking around entails.

For example, if this is your first job and you’ve only been working for 4 months, you likely have not seen enough highs and lows of the job to really understand it. As a result, when you experience a low in your job, you are more likely to believe that the perceived benefit of staying is far less than what it actually may be.

If work isn’t amazing, a great first step is to candidly discuss your concerns with your manager and brainstorm a plan to work on more engaging projects. To make this conversation successful, come to the meeting with realistic solutions, not just problems and an entitled attitude.

Lastly, it’s worth looking into internal transfers, because you may find an incredible opportunity within your company.

In general, I think people don’t try hard enough to remedy the situation at their current job. Try your best to understand and shape your future in your current role before looking for the exit.

Friction of changing jobs

Lastly, friction is an important part of this equation because it prevents people from changing jobs when an opportunity slightly better than their current situation arises.

Friction of changing jobs includes the hassle of searching for opportunities, interviewing, joining a new company, rebuilding relationships, etc. This can be an exciting new start to some, but if you’re content in your current position, this can also feel like a hassle that’s not worth your time.  

When it doubt about your current situation, refer back to my formula from earlier.  

Perceived benefit of leaving  > Perceived benefit of staying + Friction of changing jobs

Is the perceived benefit of leaving better than the perceived benefit of staying plus the hassle of changing jobs?

To inform your comparison of opportunities, it’s helpful to consider a range of factors. Below, I’ve outlined the important factors I consider when evaluating an opportunity, along with those I consciously try to avoid.

I’ve listed them in no particular order, since the importance of each factor is a personal decision.

Factors to gauge opportunities

1) Skills and pace of learning

Are you building concrete skills that are valuable for your career goals? How quickly will you learn relative to your pace of learning today?

Positions in high-stress environments like professional services (consulting & banking), rotational programs, high-growth companies, etc., are all great environments to accelerate your pace of learning.

On the other hand, a cushy job at a large company might not push you to grow as much -- which I believe is crucial in the early stages of your career.

2) Compensation

This is usually the first consideration that comes to mind for most people.  

How does total compensation (not just base salary) compare to your current position? How does it increase over time? Are people promoted quickly upon strong performance?

As mentioned earlier, compensation is an important factor, but I prefer to prioritize skill development.

3) Alignment with interest and goals

Is the new opportunity going to help you achieve your long-term career hypothesis? Will it provide optionality for future career opportunities?

If not, do you at least find the work fascinating and worth learning for 40+ hours a week?

If the answer is no, this is probably not the right opportunity for you. Try to spend your time on work that will energize and excite you.

4) Work environment & culture

There’s a tendency to think about culture as soft, intangible, and therefore not important. But this couldn’t be further from the truth. In fact, I would personally place culture as one of my top criteria.

Culture = your day to day happiness.

A company’s people, values, way of working, and decision-making process will deeply impact your happiness and fulfillment. Here’s a guide I wrote with questions to evaluate a company’s culture.

5) Your manager

A common adage for making career decisions is to find a manager you respect, build a strong relationship, and follow them throughout their career.

The thinking is that if your manager is top-notch, she will continue to be promoted and find interesting opportunities. Simultaneously, by having a strong relationship with her, she will include you in these opportunities and pull you to the top.

There are countless case studies of CEOs, executives, and government officials who followed other successful people and fast-tracked their careers.

Regardless of whether this is the approach you are taking, it is worth considering an opportunity with a very strong manager.

Factors to avoid when evaluating a new opportunity

Here are some common factors I notice people heavily rely on to make decisions. It’s not that these are bad, but they shouldn’t be your primary focus because they are largely related to external validation.

I don’t believe that external validation will meaningfully help you feel happy and fulfilled in your career.

1) Making more than your friends (compensation)

For some, it’s important to make more than their friends. However, compensation can quickly be tied to self worth and become a slippery slope when making career decisions.

2) Peer pressure and prestige

In college (and beyond), there is peer pressure to work for certain prestigious companies or industries.

Prestige is a powerful form of external validation. It gets people to optimize for validation over their genuine interest in a job. This is usually in direct conflict of the hypothesis-driven approach to career discovery and decision making.

It’s nearly impossible to completely ignore prestige, but I find that being aware of it is incredibly helpful when making a career decision.

By acknowledging the role prestige is playing in your excitement for an opportunity, you can force yourself to reflect on whether you would take this role if the prestige wasn’t there.

Again, you are going to be investing thousands of hours a year in this job. How much does it really matter what others think about your career path?

3) Perks

You may have heard of the ridiculous perks of technology companies in the Silicon Valley.

The fancy chef-prepared food, stipends for massages and gym memberships, fitness classes, unlimited time off… it’s all completely true.

I know it sounds very exciting, but you get used to the perks of a company very quickly. After the glamor fades, all that’s left is the fundamental parts of the job that I mentioned earlier (culture, manager, skill development opportunities, etc.).

Perks are never a substitute for that, so don’t consider them too much when making a big career decision.


When thinking about leaving your job or choosing between multiple job opportunities, brainstorm your list of the following:

  1. Guiding principles
  2. Important factors to consider
  3. Factors you want to ignore

By having a customized framework for yourself, you will become more confident and able to make informed career decisions.

Lastly, remember that it’s totally okay if your first job is not optimal. It is only the first of many jobs you will have.

Over the long run, it’s more important to learn how to find and make strong, consistent career decisions than landing the perfect first job.

Finally, thanks to everyone who emails me stories of their successes and challenges. I love reading your emails and they often inform the topics I write about.

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