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  • Mark Olivito

40 Life Lessons @ 40

Updated: Mar 12, 2022

My birthday being the last day of the year has always served as a springboard for a bit of reflection. 8 years ago I experienced the "big 4-0" and my wife sparked an idea for a post on my blog Hustle or Bust: "Life lessons at 40."

leadership blog, hustle or bust

I've copied in below. At that time I was at a life cross-roads, contemplating taking on over $11mm of debt to chase a life long dream of buying a company, while being very satisfied with 8 great years at a wonderful company and co-workers I consider lifelong friends. It was an easy write, but challenging time.

With 8 years in the rear view mirror and re-reading this I was reminded of a couple things:

1) My biggest life lessons came through DOING, not THINKING about doing.

2) The parallel between the pillars of the Brick by Brick Apprenticeship program and these life lessons are strikingly similar.
* Decisions, mentors, relationships, goal setting, experience, attitude, drive, reputation building, results are hugely important. Learning to get them right and improving in each area really matters.

18 years old can be a confusing, exciting, scary time, all wrapped into one. Like the front page of the Brick by Brick website says: NOBODY has all the answers to happy and successful life. But many people have different levels of experience for what works and what doesn't. Here's some of mine.....

The Life Marathon

  • Where you start does not dictate where you finish. Some are born with silver spoons; some are born disadvantaged, behind the proverbial 8 ball. Move forward from where you are. Or don't and you'll finish even worse.

  • Key life decisions matter. Take the time to get them right, with the information you have, but you'll never have ALL the pieces.

  • In a marathon (life) of competing, growing, Hustling, make sure you enjoy the ride. Even the rough parts of the journey can be appreciated.

Training (Learning) & Outlook

  • Mentors matter. A ton. Seek them out. Better yet, do a great job, be a solid citizen and they will seek YOU out.

  • Experience is a valuable teacher. It also tends to be expensive. Hence, the need for mentors to prevent you from scraping your knees, to learn from THEIR experience.

  • Never take for granted the value of the school of hard knocks. Translation: Learning from the street (where the action happens) is pretty darn valuable. Give me someone who conquered the streets and I'll place my bets on them any day of the week.

  • Relationships matter. Solid relationships in all areas of life will be a "force multiplier" to your happiness.

  • True, great friends are worth their weight in gold. If you can fill one hand with them over the course of your life, consider yourself lucky.

  • Family: Few things in life are as simple and none are more important. The key word that makes Family's magical? TOGETHER


  • Your Example is your most powerful motivator for others, set a great one.

  • Respect needs to be earned. No easier way than getting dirt under your nails with the people you lead.

  • Leadership is a contact sport. It gets messy. There tends to be real conflict and confrontation. If you fear or avoid conflict, find another sport.

  • Expect the best from people. The overwhelming majority of people (98%+) have sound, noble intentions. They want to do a good job and win, a leader's job is to help them, be a partner, and celebrate when it happens.

  • Not EVERYONE has noble intentions. They may burn you, betray your trust, and hurt others in the process. These will be rare occasions, but it will happen. When it does, FIGHT the urge to become cynical and unwilling to trust. The downside of being cynical is greater than the safety it provides.

  • Magical words: "What do you think?"

  • Smiles don't cost a thing.

  • Thank Yous don't cost a thing either.

  • Magical Skill? Listening. Play back what you hear to get it right. Then follow up with ACTIONS.

  • Goals are you compass. Write them down. On a flash card, and carry them with you, Old School style.

Marketing & Business

  • Brand names in life matter. Strong brands matter to people. The most important name in your life? Yours. It's called your reputation. Protect your reputation. "Build it" over time, but never do anything to damage your good name.

  • Nothing happens until someone sells something.

  • Facts are stubborn things. Too many people shoot from the hip, because it's easier and requires less digging (research). He who has the facts, tends to lead.

  • NEVER miss a Sea Change in your profession. You stack the deck against yourself when you ignore sea changes.

  • Getting EXPECTATIONS defined is half the battle. Delivering is the other half.

  • Technology is the great accelerator of our time. The biggest difference maker in the world is not technology however, it's PEOPLE.

Life Choices

  • Living a fulfilled life comes down to a series of intentional choices. You control 100% of life's major difference makers.

  • Attitude is a choice. Choose wisely and it will be recognized. The reverse is also true

  • Optimism is a force multiplier. It injects oxygen.

  • Pessimism, SUCKS oxygen.

    • Use the WAKE UP test to check your level of optimism.

  • Time is life's great equalizer; we all have 24 hours in a day, that never discriminates based on who you are or what you have. Invest your time wisely.

  • An Emergency fund should be rule #1 in the world of $'s. It's not just for emergencies.

  • You have 1 body in life. Respect it, take care of it. It will get stronger if you push it. If you don't, it will get weaker over time.

  • Getting your workout started and finished before the sun rises is a major difference maker.

  • There's a reason people don't take advantage of the head start/start early principle. It's hard.

  • There's always room for people who take on the HARD work.

  • The secret to building TRUST is doing what you say you will do. And repeating. Consistently.

  • There's a reason why your third grade teacher made you check your work before handing in the test. It's MORE important when you're getting paid.

  • Very few people deal with life or death situations. Don't take things so seriously. Especially yourself.

  • The mirror test is life's great acid test. When you look in it, are you happy with what you see? Your day's effort? The decisions you've made? The impact you've had on people? If yes, sleep well. If not, you can wake up in the morning and start making different choices.

Those were MY life lessons. What are yours?

It is Never too soon to start writing down what matters to you, what you've learned and what it means for your future.


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