A simple question
The last few years have been crazy, and no wonder there’s a ton of folks thinking about making job changes right now. I know this since I’ve been getting the calls. Often the conversations open with a laundry list of different companies, roles, and compensation packages. Every opportunity is completely different and hard to compare. There’s got to be a better way to organize your thinking about these opportunities.

Here’s my favorite question to ask:

“What do you want to be your next next job? And why can’t you get it right now?”

And then, of course, you work backward from that. This is the “Next Next Job” framework for thinking about career moves, particularly in the highly chaotic situations that we find ourselves in today where there are many many opportunities across different industries and company stages. This reflects the very natural flow of the recruiting process, where recruiters and colleagues often make referrals across a wide swath of companies that are making. It’s always fun to talk through the various roles, but also it feels chaotic.

I know how it feels because, of course, I’ve faced this exact situation before.

The Next Next Job is an evaluation framework that I used myself many years ago, to make an important decision: As an early 30-something-year-old, at the tail end of a startup adventure that had gone awry, I had a big decision to make. A few months after putting my startup team/myself on the market, I was choosing between several very strong acquisition offers at pre-IPO startups. Each had its idiosyncratic benefits — some of the team cultures were a better fit for me than others and in others, I had a stronger connection to the founder. The packages were also very different. It was an emotional rollercoaster to meet dozens of companies over several months, and then need to choose amongst them.

It was tempting to pick based on a gut reaction, but I felt like there must be a better way. I sought a more analytical approach to augment the rollercoaster. I have tremendous gratitude to my close friend Bubba Murarka who coached me through all the conversations. Once the offers came in, he challenged me to stack rank the opportunities based on my “next next job” — almost a throwaway comment — but something that’s stuck.

How to answer a simple question
Let’s go back to the question – “what’s your next next job, and why can’t you get it today?” — it’s straightforward to ask, of course, but surprisingly hard to answer. Often we don’t know what we don’t know.

The first is that we often don’t know what our next next job might be — after all, if it’s unclear what the next job is, speculating about the next next job seems even more nebulous. Yet there’s an advantage here because you can make a few pretty big buckets of next next jobs. Or you can at least start to, based on what you know today.

It might look something like this:

  • 50% – Become a startup investor
  • 30% – Start another company
  • 10% – Join a high-growth startup as a C-level exec
  • 10% – Random stuff? (Switch into a new cutting-edge industry, become a blogger/writer, etc)

For someone who’s earlier in their career and the product management function, the goals might be more focused on becoming a first-time manager of PMs, becoming “employee 1” of a high-potential startup, or getting accepted into YCombinator, or something like that. Others might be thinking about transitioning from a non-tech role into a tech job or maybe going from a non-product role into becoming a PM/designer/eng.

Of course, sometimes it’s not obvious what other roles might be interesting or appealing — this in itself can be a useful thing to focus on when meeting with mentors and colleagues in the industry. But assuming you have some pretty big buckets to think about, the next step I’d encourage you to do is to pick the top 2-3 of these and do your research. Meet as many people as you can who have your next next job. What were their career paths? What did they need to accomplish before they could get the job? And you can ask them straight out — “what are the gaps in my skills that I need to fill, to get your type of role?” Keep asking questions and meeting people until the answers start to sound pretty similar, and the delta of new information decreases substantially.

Sometimes there’s a shortcut (and sometimes there’s not)
A funny thing sometimes emerges, particularly for people who rank “start a new company” as their next next job — it turns out they’re already qualified. Some of these jobs have high degrees of emotional baggage, because of Imposter Syndrome and not feeling ready. But the reality is, sometimes people over-prepare for a future job out of a deep sense of risk aversion. These are folks who are getting as credentialed and qualified as possible, rather than jumping in. These are the “wantrepreneurs” who are wasting their time getting multiple advanced degrees, working at all the top companies, and who are often very smart — but just can’t bring themselves to actually do something on their own. Usually, when this is one of my friends/colleagues, I try to talk them into taking the largest degree of risk possible 🙂

On the other hand, often the next next job isn’t attainable and it’s for good reasons. Maybe you’ve only worked at a series of failed startups, and you need a “shiny” role or two that helps add some credentialing. Or perhaps you’re in marketing and interested in becoming a PM but aren’t yet close enough to the engineers and the technical details. Perhaps you’ve never managed anyone, and want a role to demonstrate strong managerial ability before jumping into a team lead role. Identifying these gaps can help form the basis for evaluating potential job opportunities — which ones help fill them better and faster.

Gaps might encompass a number of things — skills, but also network, experiences, mentors, and ideas:

  • What new skills do I need for my next next job?
  • Is there a new network of people that would help me?
  • Are there experiences that I need to demonstrate to land the next next job?
  • Which mentors do I need, and how would I meet them?
  • How do I get exposed to the ideas that might inspire me in the future?

Understanding these gaps are great, but that’s just playing offense. A “superpower” is often important, and there are superpowers that are so important that they overcome an imperfect set of gaps. I sometimes talk to folks who are interested to get into investing, and in the end, you can check off every skill on the list, but unless you have a specific superpower I care about — getting in the flow of new startups we’d be interested to meet and invest in — it doesn’t matter how good your analytical skills are, or that you attended fancy schools. If you have an incredible network of founders who seek you out, you can learn some of the other skills. For your industry and specialization, figure out the superpower that might trump everything else. Think offense (building up a superpower), not just defense (filling in gaps).

I want to give an example. For someone interested in investing as their next next job, and have substantial internal-facing roles at successful startups, I often find the list looks something like this:

  • The next next job: Become a professional investor
  • Gap: Need to develop a personal brand for other external-facing networks
  • Gap: Haven’t done any angel investing
  • Gap: Need to develop opinions on cutting-edge spaces
  • Potential superpower: Get in the dealflow of recent spinouts/alumni of my prev companies

Again, this is just a hypothetical example – you can run your analysis and figure out what you need to do to close some gaps and develop a superpower. Of course, if you are tracking 2-3 options for next next jobs, you might find that a few gaps appear and re-appear. That’s great! This means the next role that helps you develop against that should be weighted more heavily.

Evaluating the grab bag of jobs
Now we can go back to the original question — “what do you think of XYZ as a company, and should I take this ABC role there?” The approach then becomes more obvious. First, you need more than one option. Go run a process, meet enough people, and look broadly at enough companies that you have different options to compare. Building up these options — while the opposite of instant gratification — will mean that you can truly make a good decision.

Then work backward on your options. Which ones are best at filling your gaps, and what will help you develop a superpower? Or if none of the options do much, then be patient. Develop more options. I think a lot of the reason why we often see a long series of 12-month stints on resumes is that we live in a world of instant gratification — whether that’s short videos for instant entertainment, on-demand food, groceries, cars, or online dating. But when it comes to making a big career decision that might commit you to work somewhere for (ideally) multiple years, the quality of the decision is important. Taking your time is key.

Of course, in the end, this big decision is very emotional. I really believe that. There are a ton of little things that go into getting excited about a new role: You’ll need to vibe with your manager, and you’ll want to like the work. But at the same time, having a bit of an analytical framework behind your decision will help. It might ultimately be 80% emotional and 20%, but I think that’s still better than 100% emotional rollercoaster.

To wrap up my story, almost ten years ago, I decided to go to Uber rather than the other very good options on the table. The background was that I knew it was likely I’d want to become an investor one day, and that pointed toward Uber as the right choice. The theory was that Uber would be a great place to meet future founders, would have problems at scale, and would be a very interesting place. And boy, was I right about that latter point 🙂 It did OK on the other things I cared about — the scope of my role, the compensation package, etc — but I chose not to optimize for that. I knew it wasn’t my forever job. It was a stepping stone to the forever job I’d try to gain in startup investing, many years later.

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