My most brutal year yet

Hard-won lessons from 2024.

Howdy GirdleyWorld! 

I hope your 2024 was better than mine. The silver lining? I learned a ton.

  • 21 things I learned from the most brutal year of my life

Let’s do it!

I turned 50 this month. But I had to check the calendar, because it felt like I was turning 100. 

2024 was the most brutal year of my life. 

Sleepless nights, emotional hurt, ending of decades-long relationships, betrayal, physical symptoms of stress — the whole entrepreneurship rollercoaster.

I have seen investments and deals underperform, shut down a business, replaced four CEOs, and spent a lot of time fixing my companies. 

For a few months, every Friday morning brought yet another costly problem.

I started waking up dreading the end of each week – to the point I had trouble eating. It was ridiculous. (Though I got lean as hell :-/ )

Thankfully, I’m getting a little distance from it now. 

So here’s what I learned.

Managing people

  1. It’s easy to get complacent with key employees. However, every job isn't static, from the CEO to the janitor. Someone can start great, and the job will change underneath them.

  2. “Trust but verify” is easy to say but hard to do in practice. Many will interpret the “verify” part as a lack of trust, which you must ignore.

  3. When an employee accuses you of lacking integrity or intentions, separate from them immediately. Same for catching them lying or arguing that something is true that contradicts what you’ve seen with your own eyes. Trust, at that point, is gone and won’t ever return.

  4. You will have to hurt people’s feelings in business and life. I’ve made the mistake of being too nice too many times.

Dealing with stress

  1. Don’t entirely cut inspiring things out of your life when stuff gets hard. You need them to stay sane.

  1. If you’re stressed, take a day off to recharge. Medication can and will help if you can’t calm down if necessary. There’s no shame in it.

  2. The brain has limits and is flawed. Stress and anxiety will weigh on you and can put you into a doom loop. Getting help from therapy and even drugs is ok.

  3. Don’t be ashamed that you’re going through hell — even if you feel stupid because it’s your own doing. The best therapy is sharing what’s happening with trusted friends and family.

  4. It’s all relative. I had lots of low points this year. Then, I’d hear about a neighbor who had just been diagnosed with cancer, or someone who lost their spouse way too young.

  5. When you feel high anxiety, shift from a “what if something bad happens” mindset to an “even if that happens, I'll be okay” approach.

  6. Find a way to get little wins when things are going poorly, even if it’s tidying your office. Get back on a winning streak.

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Building businesses

  1. In business, where there is smoke, there is always fire in your organization. Your job is to rush to it and find out what is happening. Then act fast.

  2. EOS is a sound system but doesn’t fix poor personnel fits or bad leadership.

  3. Tailwinds will become headwinds quietly and sneak up on you. The things that originally made your business thrive can go away one after another, dooming the company.

Lessons in money

  1. If you raise money from people, ask if the investor is writing a larger check size than usual. If they are, they’ll be the first to take it super badly if things go poorly.

  2. Have three times as much cash in reserves as you think you need. Things can and will get worse than you imagined. Expect rainy days, but prepare for Category 5 hurricanes.

Personal lessons

  1. Things that get broken over the years will usually take years to fix. Be patient.

  2. If you’re going to have a chief of staff, they need to be trusted completely and have access to everything to do their job well.

  3. Don’t hide things from your spouse. If you can’t cry in front of them, you’re holding back too much. (If I had to pick one thing from this list, this would be it.)

One thing that didn’t go wrong this year: my company Near.

They’ve been kicking butt. They’ve got tons of happy clients, saving a ton of money, and breaking tons of records with amazing Latin American talent. 

Super proud of the team over there. 

Book a call with them today — this link will save you 5% on your first hire.

3 things from this week

  • Appetizer: Business Twitter is still fangirling over Jesse Tinsley acquiring Bench. Love it. If you missed it last week, check out our interview with him (including his acquisition strategy)!

  • Main: Goal Setting for Entrepreneurs – my latest lecture is up YouTube. Check it out! (Even better — join our planning cohort at Scalepath!)

  • Dessert: Spotted (or not) in the wild.

That’s all, folks! Thanks for reading, and have a great week.

Michael

P.S. What did YOU learn this year? 

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