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Chris Ming

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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:

Everything is always changing. New roles and functions are always emerging, the underlying knowledge for tech is accelerating, nothing is a linear path. As a result, navigating this part of the journey is chaotic and volatile (source).

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.” (Arnold was guilty of it, too.)

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

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

Let’s jump in.

For most people, goal setting is a waste of time.

Why? Because they don’t track their progress against those goals. If you’re going to set goals, keep yourself accountable. Here is the recap of my Q2 2022, the good, bad, and ugly.

Today, I’m going to share my favorite tips and tools for working remotely. This list has been refined after:

  • After 9 years of remote work
  • In 7 different roles
  • Across multiple industries

Only 16% of companies are fully-remote businesses[efn_note]https://www.apollotechnical.com/statistics-on-remote-workers/[/efn_note]. Companies will spend the next 20-30 years addressing working remotely challenges. This means it’s our responsibility to create a great remote work experience.

By optimizing how you work remotely, you’ll drive more impact, get promoted faster, and earn more money. Plus, life is just more enjoyable.

The problem is most people treat remote work as working at the office… but at home. It’s not. Instead, they need to rethink every aspect of their work processes, routines, and cadences from a remote-first mindset.

Note: if you’re looking to land your first remote job, check out my article here. And if you’re trying to break into tech, read this first.

7 Tips for Working Remotely (That No One Talks About)

Remote work is a skill. The better your skills, the more successful you’ll be in a remote-first career. Here are 7 tips to improve the skill of working remotely:

This is a recap of the first quarter of 2022.

In my 2022 planning post I said:

I’m focused on building my audience, career, and relationships for Q1 of 2022. This is probably an indication they’re going to be the focus for the year.

This quarter I reached the blog traffic goal. I missed on the newsletter and Twitter goals.

For the second quarter, here’s what I’ll tackle and the order of priority:

  • (High) Build processes to write and engage on Twitter and LinkedIn daily
  • (Med) SEO optimization for 3-5 blog articles; write at least 1-2 SEO articles
  • (Low) Define the value proposition of the newsletter; reposition opt-ins

Let’s dig into how things went. Plus, plans for next quarter.

(How did you do this quarter? Would love to read or hear about your retro!)

My first thought when hearing about the 1000 Hours Outside Challenge? Sounds great, but that’s impossible for us.

Both Amy and I worked — a lot. Our kids spent the entire day in creche (daycare). We lived in an apartment in a city. There was no backyard we could chuck the kids into to leave to their own devices.

But moving to Dublin, Ireland had an unintended consequence: more time outside. We had no choice. With no car, we either walked or took public transportation. Instead of driving everywhere like we did in Albany:

  • We walked 2km to get groceries at SuperValu
  • Rode bikes into the city center to catch a movie
  • Spent hours at playgrounds in Phoenix Park, Inchicore, and Malahide

At the end of 2021, Amy started talking about the 1000 Hours Outside Challenge. Despite my initial skepticism (1,000 hours?! 3 hours a day?) we started tracking our time outside. We realized with existing habits, we were already tracking close to that goal.

And we loved the lifestyle.

Should you set goals?

The problems with goals are well-documented.

  • Goals end. When they do, people feel empty. Then they revert to their previous state. Land your dream job? A week later you’re back on LinkedIn. Lose 30 pounds and celebrate with pancakes. Accumulate a million in the bank, and wonder why you’re still not satisfied.
  • Goals delay happiness. By setting goals you’re saying, “when I reach that milestone, then I’ll be happy.” Happiness is a state only the future you deserve. The current you? Back to the grindstone.
  • Goals incentivize short-term thinking. Goals lead to tunnel vision. You’re tempted to hit that goal – no matter what. So you start cutting corners and juking stats.

There’s a popular line of thinking: instead of goals, we should focus on habits and systems. Habits and systems are better because when done well, they happen automatically. Little or no will power required! Work the system and the system will work for you.

​​There’s a great Jerry Seinfeld story. It goes like this:

A young, up-and-coming comic name Brad Issac asked Seinfeld for advice.

Seinfeld told him to be a better comic, he needed to create better jokes. The way to create better jokes was to write every day.

“He told me to get a big wall calendar that has a whole year on one page and hang it on a prominent wall. The next step was to get a big red magic marker. He said for each day that I do my task of writing, I get to put a big red X over that day.

“‘After a few days you’ll have a chain. Just keep at it and the chain will grow longer every day,’ Seinfeld said.  ‘You’ll like seeing that chain, especially when you get a few weeks under your belt. Your only job is to not break the chain.’”

Consistency over intensity

The message: Consistency wins! Consistency over intensity! Don’t burn out, don’t overextend. Keep showing up every day.

I had a different email planned, but last week I tested positive for Covid which threw that off schedule. Fortunately, my symptoms were mild, and after self-isolation ended, I re-joined Amy in the not-so-delicate juggle of childcare and working from home. It was a flashback to April 2020, our first foray into lockdown life.

Despite having both Oliver and Annabel this time (AND one-third of the living space we had in Albany), everything felt… easier.

Part of this is attributable to greater certainty around Covid:

  • You can expect mild symptoms (if you’re reasonably healthy)
  • You can expect lockdown to end (eventually)
  • You can expect access to essentials (remember when finding toilet paper was like a Banksy sighting?)

None of this was true 18 months ago. As difficult as it is, we’ve made progress. It’ll continue to get better.

If you only have a minute, here are the takeaways:

  • Investing is emotional. I made my second real estate investment. It was more of an emotional decision than a numbers-driven one. In my opinion, this is OK (even normal) but don’t fool yourself thinking otherwise.
  • Upstate New York and self-funded. The investment is an apartment community in upstate New York. I funded it with the money after selling my house and from savings. Ideally, this investment adds a revenue stream that funds my Business system target.
  • Play your advantages. Most retail investors do not have an analytical competitive advantage. But you can have a behavioral competitive advantage. Counterintuitively, this usually means doing less, e.g. less trading, less complexity, etc.
  • How to increase your behavioral advantage? Understand your asset allocation, automate your saving & investing, have a long time horizon, and protect your downside.
  • Survival. The cornerstone of any strategy. You have to stay in the game long enough to win it.
  • What game are you playing? The game of money is fascinating, but the real game we’re playing is the happiness game. And happiness not having everything you want, but wanting everything you have.

I made my second real estate investment at the end of 2022. Once I started to document my thought process, I realized how much my investing was an emotional and intuitive decision, not a math-based decision.