31 Essential Life Lessons I Finally Grasped After Screwing Up Time and Again

This is not a complete list of my screw-ups. I simply had to choose a number and stick with it for this article.

Tree, wall, and birds. Strip Mall, Phoenix, Arizona. Photo by Don Giannatti.

So I chose 31. Seemed legit.

In life, we all have to stumble upon lessons the hard way. Some of us more than once. Though we’d rather wish we could learn from other people’s mistakes, it’s often our own experiences that teach us the most valuable insights. Here, I explore 31 indispensable, indisputable, painful, and occasionally expensive lessons that, although learned through trial and error, have shaped the course of many lives. Including mine.

1. Embrace uncertainty:
   Accepting ambiguity, uncertainty, and even those WTF moments allows us to embrace change and, strangely, live a less stressful life. No one is promised anything, nothing is owed to us, and nobody knows what the next hour brings let alone a lifetime. Life is better when you choose to live it with a sense of wonder and surprise. Of course, surprises can also be WTF moments. Just sayin’.

2. Maintain boundaries at all costs:
   Establishing and respecting personal and professional limits helps maintain an insanity-free existence. Hopefully. Too many people want too much of each one of us. It’s OK to put up a wall every now and even hide in dark hallways from those who do not understand the “Do Not Enter” sign we literally wear around our necks.

3. Take care of yourself:
   Treat mental and physical well-being with urgent importance for a more balanced, and less hectic, life. For mental health I read, play music, and make photographs. For physical health, I work out, walk, and ride my motorcycle. Hey, don’t start with me, motorcycling is proven to burn up 80 calories an hour, baby. That’s science.

4. Master the art of saying “no”:
   Learn when and how to politely decline requests to protect your time and energy. Or maybe not so politely if need be. Believe me, this one will make a difference. So many of us are people pleasers and we think it is our little burden to be everywhere at all times helping everyone who says they need it. You need to say no. Say it again. Say it until it feels right.

5. Seek help when need it:
   I was always that “If you want it done right, do it yourself” guy. I needed to be sure it was done my way, on my terms. And that will burn your ass out. Don’t hesitate to reach out to others when you need some help. Most people will be ready for you. Some won’t. But that’s life.

6. Emphasize quality over quantity:
   In relationships, financial situations, investments, etc… A few high-quality friends beat a clown car full of hangers-on, wannabees, sycophants, and losers. Fewer things of higher quality make life simply sublime.

7. Emphasize quantity over quality:
   Wait, what? I’m talking about when you are building your business or portfolio. Make an absolute crap ton of photos in order to get a few good ones. Write a million words to find a few good posts. Design 2563 logos and you’ll get a few you love.

8. Accept and learn from failure:
   Failure and I are old friends. I use setbacks as possible positive opportunities to grow and improve. I cheat the doom of failing by turning it into a learning situation, and then laughing in its face. I once had a partner steal a quarter of a million dollars from me. I learned a hell of a lot from that experience. A hell of a lot. (Ask me for suggestions if you are setting up a partnership… seriously.)

9. Cultivate patience — and impatience:
   Work to develop the patience to navigate challenging, and sometimes very upsetting situations with grace. But be impatient enough to keep on pushing to be better every day. I practice impatient patience.

10. Listening can be as powerful as speaking:
    Listen to what is being said and digest it a bit before blurting out an answer. Many a client was served (and gigs saved) when I would take a beat and give a measured and well-thought-out answer to what may have been a terrifically stupid question. Too often we are not listening to what people are saying, we are instead listening for our opening to speak. Listening may reveal the subtext behind the words and they can occasionally be far more important.

11. Prioritize your values:
    Ensure your actions align with your values because you will undoubtedly come up against situations that do not align and you will have to make a choice. I turned down a few big gigs due to not being interested in working with the client’s (low) values. Integrity you feel so good you positively glow.

12. Live in the present:
    Unless you got a guarantee (written, and in ink) from the ‘big guy’ that you indeed have tomorrow to look forward to, make the most of the current moment. And c’mon, stop dwelling on the past or that incredibly stupid thing you said to someone you barely remember back in 2012. Nobody cares, dude. Today is the most important day of the year. Treat it as such.

13. Embrace vulnerability:
    This one was hard for me. I struggled with it a lot. Allowing yourself to be open and genuine and to form deeper connections with others can be a bit scary for some of us. Give it a shot. Go slowly and you will find it works pretty well. I am a work in progress on this, so I live with the struggle.

14. Practice empathy:
    Put yourself in others’ shoes, especially if they are Faragamos. What, no jokes here? OK, look, to better understand other people’s perspectives and emotions, you have to figure out why they have them and understand where they are coming from. We call that empathy and it is a good thing.

15. Forgive yourself and others:
    “Release resentment to foster inner peace and more harmonious relationships”, the self-help gurus say. And I know I should do this more. I have worked it out in a lot of situations and I understand the healing property of it, I do. But there are still some deep resentments that I am probably gonna let live. They don’t hold me back, but instead, push me forward. Not saying that is a good thing, just keeping it honest here.

16. Pursue your passions:
    Dedicate as much time and energy to activities that bring you joy and fulfillment as you can. We have to create our life, it is not pre-ordained nor are we entitled to it. Do what you love as much as you can. In the end, it is what will sustain you.

17. Take calculated risks:
    Embrace the fact that you will encounter challenges or situations that may seem too good to believe. Or too awful to wrap your head around. You have to figure out how to turn those challenges into opportunities, and that occasionally takes risks. Risk is good. See number 8 for more clarity. One of the most important parts of risk-taking is simply to not be stupid. We can all muster that up, right? Right? Ask for help if you need it.

18. Set realistic expectations:
    Understand your limits, and their limits, and adjust your expectations accordingly. This is so important. Almost every problem we will encounter in life has to do with expectations not being met. Either mine or yours. I have trained myself to not bear too many expectations but to double down on the ones I do expect. And I try to manage expectations of me by others so they are not blindsided by, well, reality.

19. Develop resilience:
    Work on the ability to bounce right back from adversity. Remember that thief partner? I had a choice; roll up into a ball and whine, moan and dream of devious ways to get back at him, or get back up, take up my life, and get back to work. If I had chosen the former, I would not be in the position I am in today. And I like where I am. Resilience is getting back to the thing you wanted to do and letting the other stuff run down the hill.

20. Be kind to yourself:
    Try to treat yourself with compassion and understanding, just as you would a close friend. This is also a tough one for me, but as I get older I understand the deeper meaning. We cannot walk around all day punching our stupid faces in for being human. (#8 again). It is fairly normal to fuck up. Elon bought a cesspool named Twitter and so far has only lost $22BN. But it is what we do for ourselves when we forgive those inopportune, and occasionally insane moments, that help us keep on keeping on.

21. Embrace change:
    You had better understand this one. Look back 6 months ago and find any mention of “ChatGPT”. I was shooting film when digital came out. It was the end of photography — everyone said so. I grabbed the first digital camera I could find and started finding out what all of this would mean. Change is inevitable, change is normal, change is expected. Fighting change is a losing battle. Always has been.

22. Invest in yourself:
    Dedicate as many resources as you think necessary to personal growth and self-improvement. From books to workshops, coaches to creating new work, investing in you should always be job one. Working out, reading, learning something new, traveling even… investment in the most important entity in your happy life… you.

23. Pursue lifelong learning:
    Learn something new every day. The gift of the mind is that it can expand with knowledge, and the gift of knowledge is that it begets more knowledge. I try to learn something new whenever it presents itself. And if it doesn’t, I go on the hunt for it.

24. Trust your intuition:
    Your gut. Every bad gig started with a lump in my gut. Most bad decisions have that little gnawing at the edges. I can tell you that your gut is usually right, but it won’t stop you from ignoring it. I wish it would, but that is the way of us humans. We are so easily duped. Sigh.

25. Find as much balance as possible:
    Strive for harmony in all aspects of life. And if you cannot find the harmony, figure out which notes are interfering with it. Then you can find a solution to that inharmonious element that seems to be causing all the dissonance. (But also realize that a little dissonance is good every now and then.) See Stravinsky. Or Miles Davis.

26. Practice humility:
    Arrogance is one of the least admired traits we humans embrace. Recognize your limitations and accept that you don’t have all the answers. You don’t. Seek answers but never be so full of yourself that you begin to believe your own bullshit. We all know who you are, and you fool no one. Not even Mom, truth be told.

27. Share your knowledge:
    Help others by sharing your wisdom and experiences. I had a hell of a great career, and when it came down to the time to wind that part of my life up, I began teaching those who wanted to learn. One of the things I am most proud of is how many people I have been able to help find their passion. Be a teacher, coach, friend, or confidant. It’s gratifying and important.

28. Celebrate your hard-won achievements:
    When you win, acknowledge it. Get a great gig and knock it out of the park? Be happy and grateful for it. And share that with your peers and supporters. Acknowledge every success and appreciate your hard-won progress. Have a taco and a beer. Maybe even a cigar or two.

29. Put a value on your time:
    We have far less of it than we think we do. I remember being 35. I thought there was no limit to the time I had to go. That was a blink of an eye ago. And now the future seems a lot more limited. No, you don’t have to be all worried about it, but the reality is that we got about 4000 weeks if we are lucky. And 4000 is not that much of anything, ya know.

30. Surround yourself with positive influences:
    Choose to associate with uplifting, supportive individuals. You are the average of the five people you are around the most. Choose wisely. It’s hard to shed friends who are toxic — it’s harder still to have that toxicity around you constantly. It eats at your soul. Bite the bullet and cut the ties.

31. Take responsibility:
    Own your actions and their consequences, both good and bad. They are yours. Your decisions are yours. The consequences of those decisions are yours. Not mine, not hers, not that guy over there in the red flamingo board shorts. They are all YOURS. When you own your failures, bad decisions, and fuckups, then you have full right to own your wins too. And own them vigorously, with deep pride.

Thirty-one essential lessons. Many of them learned through pain, failure, huge monetary losses, and occasionally, successes far beyond what I could have ever expected.

We call that life.

You have the power to transform your life if you want to. We all do.

We may not like having that responsibility. In fact, a lot of people will run from taking any responsibility at all for where they are and find a lot of other people to blame their problems on.

Look, take this list and ask yourself which of these you already know, and which you may need to brush up on. And if you think a couple of them are stupid and you don’t need them, then that is — well, your decision.

BTW, if you ever think about having a business partner, make sure both of you have to sign every business check. No matter how much of a pain in the ass it is.

It could save you a quarter of a million bucks.