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What I Wish I'd Known
6 lessons for me 20 years ago

If you’re reading this because you’re pursuing freedom through growing a property management business, welcome! You’re in good company.
Last night I found myself surrounded by a bunch of early 20’s guys dispensing professional advice. In that same spirit, here’s a few things I wished I’d learned a little sooner and a little faster in my professional life. I hope one of these lands for you so you can live more confidently, and with greater integrity, peace and passion this week. 🙌🏻
Nobody cares
Nobody cares nearly as much about you as you think. This is both great and terrifying. Terrifying if it matters a great deal to you what others think. If you derive your self-worth from recognition. Within a few minutes after your eulogy someday when you die, most people will be thinking about where the potato salad is. Also, nobody cares so much about your failures, unless they can make them a bigger deal than they really are so they feel less bad about themselves. And the people willing to do that aren’t really useful to you anyway.
You have unlimited lives
In this game of business (and life) you have unlimited redos. Seriously. Once you learn this and really believe it you can start making mistakes faster and more meaningfully. There was an account I just read about a ceramics teacher that divided the class in two halves. The first was to be graded on the volume of pots made throughout the term, the second on the quality of a single pot. Guess who made the better pots? The half that produced the volume, surprisingly. When you reduce the cost of failure, you try more and learn faster.
Last year I wanted to get better at being on camera. I was so stuck trying to make everything perfect, it was very hard for me to push past the self-consciousness and just free my brain and mouth up to be authentic. I was too worried about sounding smart and being judged if I didn’t. The thing that helped? I committed to posting 15 videos per day for a week straight. I made failing easier by posting them all to a random Youtube channel no one knew about. By the end of the week I had 30+ subscribers and a creepy super fan. More importantly, I stopped overthinking being in front of the camera. It really helped.
You pick your friends (so go do it)
Growing up I used to think friends had to pick me. Wrong. Now that I’m 47 I’ve learned I get to pick my friends. Guess why this works out every time? The people I am really drawn to are almost always eventually drawn to me too. It turns out I’m way more likable than I used to think to the people I most want to associate with. I used to worry I had nothing to offer, I wasn’t that funny or interesting, so why would the people I most admire want anything to do with me? Two things had to change:
I had to fully lean into my core personality. For me, this is slightly obnoxious, bombastic, in-your-face. I figured out the approach with people that both makes me laugh and is not overly rude. Now I lean into this and let people either fall in or out of it.
Persistence. You know how some people speculate our ancestors ran down animals until they were so tired they just laid down on the ground? If I want to be friends with someone that’s pretty much what I do but in a nice way.
Dan Sullivan said “I’m not interested in working on relationships, I’m interested in relationships that work.” There are so many interesting people out there you don’t have to appeal to everyone. And it’s incredible how many people you can become friends with if you just decide you want to be their friend.
Picking the right business friends is crucial
Ever hear you are the average of the 5 people you spend the most time with? I disagree. We often spend most of our time with team and others that we are helping to teach and mentor. But what is true about this idea, generally, is we become like the people we associate with frequently. Ray Hespen is one of my favorite minds in property management. One text exchange with Ray every month or two, and I can feel myself getting smarter. It’s so cool. Tiffany Rosenbaum recently shared with me about the impact of creating a board for her business. I’m so inspired by those short, infrequent conversations. They change me. Pick great business friends, get a regular thing going and it’s like a cheat code.
Here’s a variation of this: pick your boss. There’s nothing more important early in your professional life than picking the person you work for and learn from. Remember when Warren Buffet approached Benjamin Graham and offered to work for free? Graham told him his price was too high. Be that guy.
Thoughts and feelings
ARE NOT YOU. Get out of the freaking river, dude. We were not meant to be pushed and pulled by every random emotion and thought that pops into our heads and hearts. We are up and back of that stuff. If we can observe something about ourselves we are not the thing being observed. We are the observer. There’s no integrity in over-identifying with our thoughts and feelings. They can be useful at times and they can be utterly destructive at times.
Most serious runners eventually buy a Garmin watch. There’s a feature on the Garmin watch that would tell you where your fitness is. It was wildly wrong. Often. So much so that I eventually concluded (and my running friends all agreed) that it was NEVER to be trusted unless it said your status was ‘peaking’ right before a race. Otherwise, throw the feedback out. And while we’re talking about throwing thoughts and feelings out that don’t serve you… Write down the names of everyone you’ll take feedback from on a 1in x 1in piece of paper. This comes from Brene Brown and I like it. Stop being overly open to feedback from people you shouldn’t be listening to.
Don’t miss the point when scaling
Scaling a business doesn’t mean you remove yourself. It means you increasingly make a bigger impact. And often that requires being involved in the smallest of details to hold the line with values and culture. Most of my longtime readers will know my personal cell number is out there for anyone to find. It’s on nearly every one star review response. Recently a prospective resident sent me a text wanting to explain ‘her situation’. I tried showing a little compassion, still with good boundaries, and I think it went a long way.
I’m growing businesses because I care about freedom. I want to be able to do what I want with my time. What I am realizing is there’s no real freedom in hiding from a brand that is based on you as a person. There’s no freedom in avoiding difficult conversations only you can have. There’s no freedom in side-stepping what we really came for: character development. This is not either/or. You can pursue scaling and freedom AND stay fully engaged in the most meaningful (and often uncomfortable) ways.
The root
Those are some of the things I wish I had known when I was younger. In the book 10x is Easier than 2x Ben Hardy states something radical: that 90%+ of the stuff we are doing right now actually doesn’t matter. He’s right, but how do we get clear about the 5% that really does matter and do more of that? For me, investing in our leadership development is that 5%. It’s who we’re becoming that creates our biggest future leverage in all areas of our lives. T
hink of it: to do the most epic stuff you’re capable of you’re going to have to somehow convince the smartest people who are willing to talk to you to join your vision. What’s so great about you that will make them want to do that? Spoiler: it’s not your money (and you don’t have enough to pay them yet anyway). It’s a question worth considering. If you’re an entrepreneur and you want to grow, it might be the most important question you could be asking yourself aside from “where should I place this x??” 😂😂😂
Love you. Go help people do more good today.