Niket Desai's Thoughts on Changing Jobs

Updated May 25, 20226 min
Niket Desai's Thoughts on Changing Jobs

Niket Desai's Thoughts on Changing Jobs

Niket DesaiUpdated May 25, 20226 min
Niket Desai's Thoughts on Changing Jobs

I have been talking to a lot of friends and friends of friends as of late about their careers and life aspirations.

Something about being in our late twenties has awoken us from a dogged sprint in creating our careers since entering the workforce. I think it’s because we’re now seriously incorporating many changes into our lives after much experimentation.

Part of those optimizations, of course, often include a job (or situation) we’re in. Like taking on a new role, or moving locations, diving further into a field or exiting one altogether.

Here’s a few thoughts on things I’ve been seeing as people decide what to do and how they go about it.

Not taking (enough) time off between jobs

I am flabbergasted by many friends taking nearly zero time between gigs. And I’m not talking about the masochists that leave one job Friday and join another on Monday. I’m talking about YOU — the person taking about a week off instead of doing that crazy thing you should be doing. My old boss, 

Punit, often drilled this into my head:

Take an uncomfortable amount of time off between your jobs.

Many people say they don’t need a break or would have nothing to do if they took time off between jobs. Nonsense. I think we’ve grown accustomed to being in a “working condition” and furthermore think that’s a good thing. But in my view, fast starts in new roles are an easily avoidable disservice to yourself and the new opportunity.

Companies are incentivized to fill (often long-standing) hiring gaps, not help you become the best version of yourself.

By taking an uncomfortable amount of time off you’ll be able to fully reset and doing this is critical for your future performance. You can choose to travel, do nothing at all, or take care of the many cobweb errands in the various corners of your life (hopefully all three).

Perhaps these things seem trivial compared to the new gig, but what you’re doing during this downtime is internalizing all the work you completed over the past N years. Such reflection, overt or not, allows you to solidify those learnings into your day-to-day actions and thinking process. You also gain space from your old habits that were specific to that work so your mind is less inhibited by expectations and more available to think differently.

When you reach your new job you can be much more effective not because you’re rested, but you’re more prepared to accept new concepts and methods while being less burdened by “how things used to be” which may no longer be applicable.

Going from one place to another with zero meaningful downtime means you’re already operating at a subpar level and your ceiling is likely lowered.

Sometimes perceived (or not) company pressure to join causes us to shortcut our transition time. Don’t buy into it, and furthermore, be concerned if they chose you for the immediacy of your availability rather than what you offer to them as a contributor. Most “what ifs” are only in your head.

Use time between jobs as a reset and an opportunity to catalyze learnings from your previous work inside yourself. You’ll be better for it and more charged for your next adventure. Stave off fake pressure by committing to a break that is larger than you would normally feel comfortable taking. And if you really don’t like the idleness, just get to work early.

Getting your next job when you’re at the peak of your current job

A common playbook on changing jobs is to get your next job before you leave your current one. In general, I think this is mostly useful advice except in the (somewhat common) case of people looking for a new job when they’ve realized they despise their current one.

Don’t make one of the most important decisions in your life from a negative mental disposition.

Being in a job you don’t like is terrible. Getting through each day is physically and mentally exhausting which means downtime is spent simply trying to rejuvenate, instead of taking time to grow or be introspective.

And as our generation knows, getting a job in an unclear climate is daunting at best and self-worth eroding at worse.

Your best work is often mapped to when you have maximum energy and having a great time. During this period of your job you’re least inclined to search for another role.


As your happiness with a job declines your eagerness to get a different one increases. Past a certain threshold, however, your desperation will outstrip good decision-making.

The problem is that when you’re eager enough to change jobs it’s generally because of lack of happiness. We use other words like “not growing” or “my boss is a psychopath” to describe the drop on the chart. When this happens our eagerness to change roles skyrockets, but our decision making rationale and quality plummets. And below a certain threshold any job looks better than the one you have — not a fantastic long term strategy to achieve happiness.

I got the same speech when I left 30 Rock My mom like “Why you wanna leave a good job?” My dad like “Do your thing, boy, don’t stop”

— Donald Glover, “We Ain’t Them”

It’s important to be prepared before you need to make a move. At Google, employees often created and maintained an internal resume for use in internal transfers. The key was freshness by updating the document as you did your work.

If you attempt to resurrect your resume after years of working a certain job it will be difficult to remember everything you did and articulate it well. My friend Cameron is able to offset this delay by interviewing once a month. By exploring the market (even for practice) she keeps her resume fresh, understands what’s happening in market, and sees other neat opportunities she might incorporate into her current position.

Asking for time before saying “yes”

Sometimes I wish I had a nightmare during my sleep that clarified my purpose in the world. The one that scares you awake, damn sweaty, but also sets you off on a course until you die.

There’s a problem with my fantasy nightmare: nobody is going to tell you what to do. There’s no magic black car that shows up with a person that says, “This is what you’re born to do and conveniently here’s a wonderful gig for you to take.”

During the evaluation process for a job we’re often fraught with the fear of making the wrong decision. And worst of all, we’re encouraged to make fast decisions because of exploding offers or competing candidates (especially those horrible “internal” ones).

I always ask for more time when evaluating a job, especially if I know I’m going to accept it. The extra time allows for cooler minds to prevail, and also the opportunity for more information to present itself. Spend time talking to potential colleagues and your boss, as well as doing heavy research on the company and industry. Don’t let hype, money, or promises trick you.

I often like to remind people of their expected lifespans. It’s a funny number that helps me think about the use of my finite time.

Don’t you think it’s weird we feel anxious asking for 7 extra days to evaluate something we might end up spending 700 or more days on?

What does it say about hiring managers or companies who are willing to so quickly replace you based on a semi-arbitrary time constraint? If you’re worth it people will wait, but be respectful of the pressures they face.

As a counterpoint we have the Eric Schmidt scenario: “If you’re being asked to join a rocket ship don’t ask which seat.” If you have a chance to join the next Google or Facebook, it’s likely your peers or friends will be telling you to run to that job. Ask them for a few days to think about it and call them early and say you’ll start tomorrow.

But, when taking a role don’t forget to…

Clear your commitments before joining

Often people are in such a rush to start their next job they forget about life in the process. That’s okay, it happens. But make it happen less.

One thing to do before accepting a new position is to run down your calendar for the year and sort out any trips or weddings that are happening. Before you accept, it’s imperative that you get these dates on the mind of your manager (and potentially HR).

Most people will tell you not to worry about it since you’ll accrue time off — or perhaps you’re at one of those dubious “infinite time off” places. Either way, it’s important to make it clear you’ll need to be out of office during these times and are flexible in sorting out how to make that happen. If you can, try to get it in writing.

The key thing is to set expectations because people forget a lot of things when work starts. Nobody regrets working too little in their life.

Niket Desai
Niket is a serial entrepreneur currently leading product at Time by Ping and a Part-time Partner at the House Fund (as a proud Cal Bear).

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