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Life Lessons from a 50-Something Quirky Genius Living an Odd Life

Tim Denning Life Lessons

Photo by Christian Buehner on Unsplash

Life lessons can be really boring to read.

If joining the circus, becoming a musician, and starting a website that sells for millions of dollars — while giving most of the money away — isn’t an interesting life, I don’t know what it is.

Derek Sivers is a 50-something quirky genius who featured on one of the most popular podcasts of all time and wowed everybody. I read through the podcast comments and it appears that people loved how candid Derek can be, and how he is able to take complex ideas and make them simple.

Derek wrote another book recently called “Your Music And People.”

You’d think it was a book about being a musician. As usual, it’s not. His book, dedicated to musicians, is actually disguised as a book of life lessons. Here they are for you to choose from and level-up your life.


Reply to every email. It’s the greatest habit.

This life lesson doesn’t come from Derek’s book. It comes from my experience of emailing Derek for the last few years.

Derek proudly responds to every email.

He loves productivity and self improvement, yet throws all the advice out the window and responds to every email.

When he’s on podcasts that attract millions of monthly downloads, he hands out his email address. On one podcast episode the interviewer says “Are you sure you want to do that?” when Derek blindly promotes his email address and mentions how easy he is to contact.

Derek has no issues. He likes email. You can take the opposite advice to most people and do what you wish.

Every bad habit can be someone else’s good habit.

Rub your work of art in the dirt.

Derek wanted to help his friend Captain T get his music played on radio stations. He decided to deploy the power of weird.

We took each letter out to the backyard and rubbed it in dirt, then crumpled it up. Then we put the crumpled letter and CD into each black envelope, sealed it with an alien head sticker, and finally covered it with the huge label that said “Confidential! Do not open for any reason.” And that’s what we mailed to each radio station.

When the radio station employee opened the package, the letter would start with “You don’t know me, but I live in the bushes behind your station.” Derek says 375 out of the 500 radio stations played the CD on air and those who received the package still recall it today.

Make your work a little rough. Make the way you influence people even rougher. Embrace your weird.

Thinking of everything from the other person’s point of view is one of the best things you can do in life.

I emailed Derek and told him this was my favorite line from his book. He replied back and said “it’s really the key point of the whole book.”

You can be the biggest problem in your life. You will act very differently when you spend your day teleporting yourself into the imaginary shoes of others.

It’s actually impossible to fail if your only mission was to see what happens!

Failure is a mindset.

When your life is set up like a series of experiments, the meaning of what you do changes. You’re less worried about the outcome, and more focused on what could happen if you gave it a shot.

You can never predict the wild things that can happen in your life. So embrace mini-experiments and see if you can discover something special in your life.

Be generous. You’re going to see the same faces for years to come.

Grudges and revenge are deadly for a happy life.

The faces you encounter are going to keep showing up in different areas of your life. Those same faces are going to be having conversations about you when you’re not there. It’s a smart idea to be generous. People remember generosity. It leaves a lasting positive impression.

Revenge and hate do the opposite — they destroy who you could be in people’s minds who have the power to help you, or subtly change your life.

Saying you need a certain tool is just another excuse to avoid the real work.

“If only I had…” is an excuse.

Popular music group, Daft Punk, made awesome music with very little use of computers, in the early days. Everybody else was obsessed with computer software. They bucked the trend and mastered a few synthesizers and one drum machine. Simplicity made them one of the most popular electronic groups of all time.

The only tool you need is your creativity.

Get specific if you want to take action.

Derek has a friend who is a life coach. His friend said most of his job is spent helping people get specific, not giving them answers to life’s problems.

Being specific is the key to getting results.

You can’t take action on a vague goal. You CAN take action on a specific goal that is focused and has a written plan that is incredibly descriptive and goes into a lot of detail.

The tiny details make your goals a reality.

Being able to fend for yourself is real security.

Derek’s career choice of music was one many people didn’t understand. They told him a 9–5 job was more secure.

Real security is having a mindset that can get you out of anything.

As a musician Derek learned to embrace new scenarios, learn new things, live without a safety net, experiment with asking for different rates of pay, and work for many different companies (and have lots of customers instead of one that pays his salary),

A perceived lack of security helped Derek build the skills to ensure he was always secure in his own abilities, which could help him earn a decent living no matter what.

A safety net is overrated — it leads to a lack of freedom. It’s like living your life with cushions strapped to your body to protect you from the bumps and bruises — that will teach you everything you need to know about life.

Out of touch, out of mind.

The people you meet have the potential to give you opportunities you may not find on your own. Keeping in touch with people is an art worth practicing.

Call the destination and ask for directions.

Figuring out the next step to your goal can be challenging. Especially if you’ve hit a brick wall, or are ready to give up.

Derek says “Just contact someone who’s there, and ask how to get there.”

When I started out as a writer, I contacted Benjamin Hardy and asked him for directions to my writing goal. Surprisingly, with zero credibility or results, he showed me. His directions cut years off my destination. All it takes is the courage to ask someone — who has done what you want to do — for directions.

People actually love helping people.

It’s worth trying to get somebody else’s map that leads to your goal.


Powerful career lessons from a 50-something quirky genius:

  1. Talk about anything else (other than business) and just click as friends. People send business to people they like.
  2. In business it’s the opposite… if you don’t keep trying, you’re a loser!
  3. Real business is done in the follow-up, not the conference itself.
  4. Find creative ways to be considerate. That’s the best marketing.
  5. You can do things any way you want. There’s no need to adhere to norms. Norms are for businesses without personality.

Whatever excites you, go do it. Whatever drains you, stop doing it.

This is how you make decisions 10X faster in your life.

Does it excite you or drain you? Say no to what drains you. If you have to do it, outsource what drains you.

Doing all the unrelated tasks associated with your life goals sucks away your precious energy that is finite. You can love making music and have somebody else sell the concert tickets. You can love recording your music and have somebody else handle the copyright law. All the parts of your life goals that drain you can force you to give up the whole game plan.

You retain your enthusiasm for life by deciding what drains you and staying the heck away from it at all costs.

Choose what excites you to have high levels of energy that translate to a passion for life. Passion can take you far in life.


That’s what a 50-something quirky genius named Derek Sivers can teach you about life. Pick and choose from his life lessons, and experiment with them in your own life. 

Anything is possible when you take the experiences of others and implement them like they’re already your own.

Tim Denning
Tim is a thought leader in the personal development, entrepreneur and startup fields.Outside of blogging, Tim works for a large organisation helping fast moving technology companies come to Australia as well as helping Australian tech companies go to the world.

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