Want to Change Jobs? Ask Yourself This 1 Question.

A recent LinkedIn survey reported that Millennials will change jobs on average 4 times by age 32. With 55% of Millennials reportedly not feeling engaged at work, this trend does not seem to be changing anytime soon.

Over the past 6 months I’ve spoken with dozens of friends in venture, startups, real estate, fashion and finance who have entered into what some may call their “quarter-life crisis” (if Peter Thiel is right, we’ll be living past 100, so the idea of having a quarter-life crisis in your mid 20's does work) and a career/job change is top of mind. The question that I have repeatedly heard, and thought about myself, has been “how do I decide what is next?”

My goal is to help you answer that question.

A little over 2 years ago in 2014 I was coming off a failed startup and had a similar question for myself. My entire high school and college career I was looked at as the person that knew what he wanted to do (be an entrepreneur), but I hit a point where I was uncertain, fighting bouts of self-doubt and countless question marks.

A little more than 2 years prior to shutting down that startup, Category Five, I made the decision to turn down a summer offer from a prestigious Exec Search firm in order to launch the company itself. The exercise I went through to make that decision ultimately became the framework that I leveraged to make the decision to go full force in wanting to get a job in VC, and then most recently my decision to start working with Mark Gerson.

The reality is that I have no clue if this is the right exercise to go through. The jury is still out on whether or not this approach will work for myself, my friends and the other people I’ve mentioned it to in the long run, but in the meantime it has been a useful exercise in helping me create conviction in my decisions, all of which I’ve been happy with. Here’s my approach.

What do you want to optimize for?

The 4 Step Guide to Making Your Next Move.

Just like corporate strategy, people need to figure out what they want to optimize for in life. A mentor of mine once told me to think about life like a bunch of different buckets. You have one bucket of water to pour into the several buckets below, which represent the following — family, friends, community and career.

Similar to the analogy, I believe your career should be considered dynamic/fluid and at different times throughout it the amount of water in each bucket should expand or contact. However, the challenge with a career jump is that you have many more buckets to choose where to put the water in.

Thus, I like to first make a list of the various things that you may want to optimize for in your next move. I think about the categories as follows:

  • Mentorship — Who will you be working with closely? Have they been successful in the past? What level of interaction will you have with them? What can you gain from being close to them? What do other people who have worked with them say about them? When making my most recent move this was a really important part of my decision making process. Historically I’ve been lucky to work in small teams where everyone was learning rapidly along the way, but I had never worked with anyone that had scaled a company from 0–1K+ people. This was appealing to me. Additionally, I had reached out to a few mutual business friends of ours that I look up to in high regard, all of which had great things to say about my new boss.
  • Money — Some people want to choose the job that pays the most and there is nothing wrong with that. If money is what motivates you then optimizing for it may make the most sense. Matter of fact, you may have to optimize for money in order to fulfill certain life obligations. However, keep in mind that optimizing for money in the short term can sometimes hurt your chances of earning more money in the long run if you had optimized for something else.
  • Upward Mobility Internally — Understanding what the company has in mind for promotions and career trajectory is important. If you love the culture, the mission, your role and many of the other factors at a company, it’ll be important to understand whether or not you can grow there or whether you’d have to leave to achieve your other goals.
  • Level of Autonomy — Want to wear many hats and have the ability to make decisions? Oftentimes I believe there is no better way of learning. Having a great deal of autonomy can give you a lot of exposure and immeasurable experience, but it also has some additional downsides and pressures that not everyone is comfortable with early on in their career. Optimizing for autonomy requires a highly curious person that seeks out personal development and knowledge anywhere they can find it (books, outside mentors, podcasts), otherwise it can end up being a rough road.
  • Location — Want to live near your family or your significant other? How about living close to the beach or in a place where an apartment doesn’t cost you an arm and a leg? Maybe you just want to build relationships in a different city and learn a new way of thinking…Ideally you have the flexibility to live almost anywhere you want to in your 20’s because of the lack of responsibility you have (e.g. kids, mortgage to pay, etc.) so optimizing for location, or lack thereof (a la digital nomad style), can be an appealing thing for people.
  • Industry — Passionate about fashion? Maybe commodities trading? Confucius once said “choose a job you love, and you will never have to work a day in your life.” I find, and have seen, that if you’re passionate about the industry, and some other stars align (e.g. culture or mentorship), then you’ll often times work harder, want to learn more on your own and won’t feel like you’re working.
  • Title — I personally think titles are BS. However, in some industries it may make sense to optimize for title as it could help you with your next jump. Alternatively, getting a higher title at a Tier 2 type company may lead to difficulties jumping to a Tier 1 type company at the same role or higher. So keep that in mind.
  • Hard Skill Learning — Do you want to learn how to analyze eCommerce data? Model out a real estate transaction? Execute inbound marketing campaigns? Learn how to take a concept from tech pack to production? All of these are examples of hard skills. Early stage venture is a lot of fun, but can have its downsides. The reality is that many of the benefits of early stage venture are the soft skills that Junior VCs gain and the network they build. In todays workforce more and more companies need specialists and not generalists. Acquiring hard skills can be immensely beneficial to the future of your career and while it sometimes requires taking a step back in title if you started out as a generalist, it can be worth your while in the long-run as your prior experience as a generalist may make you a better manager. Reid Hoffman talks about Tours of Duty at a company. Learning as much as you can during your “Tour” will bring a ton of value to your next role.
  • Network/Relationships — The saying is that it’s not what you know, but who you know. Some jobs can provide you with exposure to people that will be forever beneficial to you and your future aspirations. I believe that identifying that value and what you may want to do 5–10 years from now is important if you want to optimize for this. 2+ years ago when I got into VC optimizing for this was a major priority of mine as I felt like it would put me in a better position to recruit a great team for my next venture and could help me raise capital easier for a variety of reasons…Now I’d try to stay away from the capital, but would love the A+ team.
  • Work Life Balance — Some jobs make it nearly impossible to have a work life balance. Bankers right out of college are often sacrificing a few years of their lives to potentially live like few others do. Same goes for Founders and many employees of startups. If working only 9–5 and then being able to unplug is important to you, or you want the ability to work remotely, I think that making sure where this lies in the order of what you want to optimize for is important. I feel like I’ve seen a trend recently of smart people jumping from startups to large companies like Facebook and Google as they wanted to make more money and achieve more of a work life balance. Each of them was very thoughtful about this.
  • Culture — When discussing management, Jim Collins noted in his book Good to Great that:
“leaders of companies that go from good to great start not with “where” but with “who.” They start by getting the right people on the bus, the wrong people off the bus, and the right people in the right seats. And they stick with that discipline — first the people, then the direction — no matter how dire the circumstances.”

I think this thought process applies to selecting a job as well. Some people spend more time with their work colleagues than their spouses. With so much time spent at work it may make sense to make this one of the top things you want to optimize for. Often times executives may join companies in different industries, but many of the people that worked for them prior will follow them. This speaks volumes to the culture they’ve built on their own team and perhaps the mentorship they provide.


Second, think about the pros and cons of optimizing for each variable for both the short term and the long run.

I find it helpful to reflect on where I want to be in 10 years as clearly as I can. Things are going to change, for sure, but it puts many of my decisions in perspective. Everyone’s situation is different. Some people will want to optimize for work life balance and money for ease of mind. Others may want to optimize for hard skill learning and mentorship because they would like to be a rising star in their industry or field of expertise in the long run. Heck, some people may optimize for network and location even if they don’t plan on being there in the long run as having access to people in that geography could be a key competitive advantage in whatever future market they’re in. Forcing yourself to think through these things and your longterm goals will hopefully help you crystalize the decision making around your next move.


Third, choose the 3–4 things that you want to optimize for.

No more than 3–4 things. I personally try to boil it down to 2 or 3 things because inevitably some of the other things that you may want to optimize for could be a natural part of your next job (e.g. money) or must haves (e.g. great culture). However, trying to optimize for more than 3 or 4 things may end up creating a high sense of uncertainty in your mind and make you second guess any opportunity that comes your way.


Fourth, create a strategy and go full force in finding the job that optimizes for those things.

Napoleon Hill stated in Think and Grow Rich, “create a definite plan for carrying out your desire and begin at once, whether you are ready or not, to put this plan into action.” Once you’ve identified what you think you want in life I think it’s important to strategically go after it with every ounce of energy you have.

I’ve seen it play out for dozens of people where they really wanted a job in one industry or another so they networked like crazy for months, read everything they could, did projects for free, became experts on stuff they knew nothing about prior and so much more. One friend of mine went from being a headhunter to commodities trader, while another became a private wealth manager after planning clinical trials for a few years. More recently with the rise of continuing ed schools like General Assembly I’ve seen people go from finance/banking to becoming product managers and developers. The options are endless.

Ultimately a major piece of landing a job that fits your criteria is going to be about timing. You may not feel like you’re making progress at times, but it only takes one offer to change your world. So put together a strategy, set KPIs around it (e.g. # of meetings set up, # of articles read, etc.) and keep hitting your goals. Eventually things will work out.

Note: It’s important to do your diligence on the role and the company that you think is the right fit during your interview process. Some things may seem great and like they fit perfect for what you want to optimize for, but it reality it may be different. Do your homework.


Making your first job change or deciding to change the industry you’re in all together is not an easy decision. By putting enough thought into your longterm goals in life and how optimizing for certain things in the short term will get you there, I’m confident that you’ll be on the right path.

The beauty of a job is that it’s not permanent. If it’s not fulfilling you can leave. Additionally, with all the resources out there today you can retool yourself to be ready for something new if you choose to. In a perfect world your self discovery will help you get on a path that you are happy with sooner rather than later, but nothing is set in stone.

Good luck with your search!

Have another approach? Shoot me your thoughts on twitter @BoatShuman. I’d love to hear best practices from other people.