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109 - A Beginner's Guide to Navigating The Messy Middle of Your Career

109 - A Beginner's Guide to Navigating The Messy Middle of Your Career

A Beginner's Guide to Navigating The Messy Middle of Your Career

August 16, 2022

The Connection | 2022.08.16 | Issue 109

Today I'm sharing 3 frameworks to accelerate through the "messy middle" of your career.Push through the messy middle quickly and you'll earn more money, faster, and be happier at your job.

What is the messy middle of your career? It's the volatile period filled with uncertainty and struggle. As Brian Balfour put it:

This period is critical. The middle makes or breaks a career.

Unfortunately, because there's no clear narrative arc (hence the "messy") people rarely talk about it. Or they put too much stock in Steve Jobs's idea that "you can only connect the dots going backward."

Instead, here are 3 frameworks to grab the reins of your career and navigate through the messy middle:

Develop a clear hypothesis for your next role
Set yourself up for success in the first 90 days (avoid these mistakes)
Capture upside and limit risk in your career

Let's jump in.

1/ Develop a clear hypothesis for your next role

Here's what I was looking for as I prepared to leave my role at Reforge:

Impact. I wanted to make decisions that impacted a large number of users.
Narrative. My career narrative has been all over the place. I wanted to consolidate my shift into technology.
Brand. I wanted some tech brand name recognition.
Stage. Late-stage but pre-liquidity event. I wanted medium-confidence for that liquidity event but still early enough to capture some upside.
Size. I wanted to work with a team of PMs, so I could learn from them (e.g. more than 5).

I evaluated 38 companies, looking at their size, stage, and business models. I talked to a dozen close friends and mentors.One company checked most of these boxes for me: Noom. I got enough signal for me to join.

My analysis was 80% correct.

I spent most of my time running experiments. I learned how to navigate a rapidly growing company that's bursting at the seams. I learned how to gather more resources, and how to advocate for myself and my team. And as a bonus, no one batted an eye when I said I'd be living in Ireland 🇮🇪Instead, we found ways to turn a "weakness" into a "strength" (helping with international QA, taking advantage of shared times zones with other engineers, experimenting with async and hybrid practices, etc.)Every company has its dysfunctions, you just choose which dysfunctions you can live with. Noom was no exception.However, there were a few critical mistakes I made early on that made it difficult for me to be successful.

2/ Set yourself up for success in the first 90 days (avoid these mistakes)

All of my mistakes fall under the same theme: prioritizing speed over investment. Here are 3 examples:

Mistake 1: I traded short-term experiment velocity for long-term knowledge.

Experimentation was Noom's differentiator. Across the growth product team we ran dozens of experiments a week. Growth PMs worked autonomously to launch, measure, and analyze their own experiments. The expectation? Ship at least 1 experiment a week. We moved fast. We broke things.Often, that "thing" was the experimentation platform and process itself. When that happened, it became much more difficult to ship experiments. You needed a deep understanding of:

What triggered a user to enter your experiment
How users dropped in and out of experiments
How can you safely add more users to your experiment (to get to sample size faster)

Early on I focused too much on the metric (1 experiment per week.) I prioritized getting experiments out over how they went out. Then as resources and traffic became more constrained, I launched experiments slower. The slower I launched, the less the team learned. The less we learned, the less wins we saw.If I could do it again, I'd invest in understanding the experimentation platform and focus less on the 1 experimentation per week metric.

Mistake 2: I moved fast alone when I should have gotten buy-in instead.

Noom was a 500-person organization and growing. It's the biggest company I've worked at. At a 50-person company, the fastest way to get something done is usually to do it yourself. I was great at that fast-twitch muscle. See a problem, fix a problem.I learned this was much harder to do at a 500-person company. All work is intertwined. There are too many dependencies.To navigate Noom, I needed to slow down and get buy-in first. Once I had buy-in, I'd get resources. With resources, I'd get things done.

Mistake 3: I didn't find an "amplifier" within the organization.

Before joining Noom, Crystal Widjaja told me: win "amplifiers" at your company.What's the difference between a manager and an amplifier? A manager oversees your work, helps you keep aligned with company goals, and helps clear roadblocks.On the other hand, according to Neetika Bansal an amplifier "typically holds a position of power in your company or organization and can directly help you improve your situation. Amplifiers can advocate for you to get a coveted promotion or even help you secure resources or means to deliver on a critical project."At a medium-sized company, to get things done you have to win the hearts and minds of the organization. Do you have someone who can be a megaphone for your work?If no, you need a methodical way of increasing your stature within a company:

being strategic about picking the right projects
get crucial small early wins
cultivating relationships across the organization from early on

Without the proper investment into these areas, it became more and more difficult to get wins. When I looked back at my body of work, I felt like I didn't contribute enough. That wasn't good for me and it wasn't good for Noom.

How to capture upside and limit risk in your career

I wasn't happy with my performance, but I hadn't kicked off a job search, either. I had only been at Noom for just over a year. There was time to turn it around.Then my friend Scott Tousley reached out about Persefoni.Sometimes you get opportunities because you run a process. Other times, you just get lucky.Scott was VP of Growth at Persefoni. He told me about the mission (enable every organization and person with the technology to positively impact the health Earth). He shared the product-led growth strategy and need to educate customers about climate change, carbon accounting, and sustainability.

The more we spoke, the more excited I got.

I learned more about the space. I wrote pages full of notes. More and more, the opportunity seemed like a great one.As always, I reached out to my board of advisors to get their opinion on the space, the company, and the offer. They help me:

Look around corners
Play devil's advocate
Evaluate risk

There were valid risks. As my friend Buford put it:

It was a fair assessment. I'm more risk-averse than ever. Becoming a parent does that to you. There's more to lose. No more

schelpping cross country to start a new industry with no foundation

for me. But there's a less obvious danger, too.

There's danger in overweighting short-term risk and discounting future upside.

Brian Feroldi put it simply:

SourceThe short-term risks were clear and finite. At most, I'd lost one income source for a few months. Meanwhile, the future upside had first and second orders.First order upside was the benefits of joining a market winner at an early-stage: salary, equity, brand.By definition, second order upside is less obvious but includes:

Learning a nascent but growing space
Leveraging this into future career opportunities
Leveraging it into future creator opportunities

Source (paywall)

In other words, when making a career switch, you can accept more risk in exchange for more upside when the risk is clear and finite.

Most career risks falls directly into this bucket.

TL:DR The messy middle is fraught with twists and turns. It also makes or breaks careers. How to navigate it skillfully:

Get specific on what you're looking for in your next opportunity
Invest in deeply understanding precisely how your business and product operates
Properly weigh first- and second-order upside with risks involved. If the risk is clear and finite, you can accept more (in exchange for more upside)