Twelve Lessons I Learned The Hard Way

I wish I had this list a long long time ago. It would have saved me a lot of aggravation. On the other hand, how many people are wise enough to take advice, even when seeing that advice result in obvious successful outcomes? Some of these seem simple and common sense, but I can count on one hand how many people I have know that follow these basic and incredibly powerful things.

The Practical Lessons

1. Before you do something over and over again (IE build 100 webpages, or 100 bluebird boxes), get the first one right. I cannot believe how many people do not do this, even after having to fix all 100 of those things multiple times.

2. Find a model. In my early years, I would start from a “blank page”. If I was creating a plan, a design, a system, a prototype, is did not matter what. At some point, likely grad school, I learned that you get better results quicker if you understand:

   1. nothing is new under the sun

   2. that’s OK

   3. you can easily find a person/group who already figured out how to do what you are doing, really really well, and allow yourself to be influenced by their work

   4. take it farther and make it your own, don’t just copy or plagiarize

   5. a great example in art is the artist Helen Frankenthaler who is considered the bridge between Pollack and later action painters - she knew and was influenced by Jackson Pollack but took her work farther and made it her own in a big way

3. If you agree to be the person responsible for following up on something (anything), the fact is, you will not remember it, no matter how important it seems in the moment. You have lots of technology at your fingertips. Set your self a reminder. One that will disrupt whatever you are doing and remind you to do that important thing.

4. Think about the future. If you do something, anything at all — most of the time you will need to do something related to that something in the future. Pretend you are that future self and ask yourself “what is it that my future self wished I had done right now, to make my life easier (and the life of my family, friends or colleagues)? Examples are things like how you create a complex product on an e-commerce website, or learn that someone you are visiting hates Pinot Noir. What happens tomorrow, next week, next month, and next year related to these things? You can make your future self have a better day if you document the things you want to remember at those points — because your future self won’t remember on their own.

5. Every single word means something different every single time to every single person. This is another one that goes unnoticed because we assume when people say they understand, they actually do understand, but if you assume that the person you are communicating with did not fully understand, and take a minute to ask them if they understand, or to repeat back what they think you said, you will be happier and more productive.

6. This one sounds like a downer, but it ends up being an upper. Assume everything is wrong. The number of times I have heard people say things like this — I assumed “they checked their work”, “they got it right”, “they used spellcheck”, “they got the changes from the client”, “they knew the date and time,” — that is a very large number. If you assume that everything is wrong and double check it, over communicate, or make sure things are understood, it not only makes people understand that you care, but they appreciate you having their back. And eventually, they get better at what they do. If you assume it is wrong, you catch a lot of mistakes, and the times everything actually is correct, it’s a nice little surprise.

7. Take the blame and give the credit to your team, partner, spouse. I learned this when I first became a director of a national company and it is amazing what it does to earn respect. And with respect comes a lot. A caveat to this is praise in public and criticize in private, a long held management axiom.

8. Create and use a checklist religiously. Tweak it forever. When I was in charge of millions of dollars of consumer packaging, my creative department was producing complex artwork for consumer goods boxes. A single incorrect UPC code could cost us $50,000 in fines from the retailer. We were making many mistakes and costing the company a lot. I introduced a simple but robust checklist and within a few months, our errors going out the door went to virtually zero.

9. Trust your instincts when you see multiple red flags from people. I am pretty much a failure at this one. The people I knew I should fire early on all ended up needing to be fired. I always thought I could guide them and mentor them to success. It never worked.

10. It takes 8. One of my mentors taught me that it takes many repetitions to make a lesson, habit, or policy stick with people. Eight was the magic number. This is related to the sales wisdom that says it takes six to eight touches with a prospect before they respond, and most salespeople give up after two.

11. Make the layouts rough and the ideas fancy. This comes from the late Stavros Cosmopolis, a legendary ad man. A good idea is far more effective than a polished layout. If you can do both, you’re solid gold. Related, always remember that a computer is like a Light Brite for bad ideas (from this fantastic set of lessons for life)

12. You almost certainly aren’t stepping on someone’s toes. In my career spanning about 40 years, I have heard many people say that they did not do something that should have been done because “I thought I was stepping on their toes”. I have never once, not one time, had anyone come to me and say “They are stepping on my toes”. I do know that there are people who do step on toes. I have a list of those people from my career. But they are outliers. To use one of these lessons from this post, this is what that “toes” phrase means.
    

Photo credit: https://unsplash.com/@quinoal