Timeless Advice I Wish I’d Followed Earlier in My Career

1. Learn to smile at trouble

“Knowing what you know now, if you could go back to when you were about to graduate from college and give yourself advice, what would you say?”

I was asked this question a few weeks ago while giving a Zoom talk to university students in the US. After I was done, one of the students suggested I expanded my short speech into a long-form article.

In addition to choosing hobbies that strengthened my brain cells instead of ones that killed them, below are the pieces of advice I touched upon along with a few extras I’ve been thinking about.

1. Learn to smile at trouble

One of my closest childhood friends has built and sold multiple 8-digit businesses. A few years ago when I asked him for his best piece of career advice he gave a hat tip to a woman he worked under when he started his career —

“I need 3 things from you while we‘re going through this troubling time. I need you to be punctual. I need you to be present. And I need you to be positive.”

Getting angry when things go wrong is the easy choice. However, the people who make an impact in the world while gaining the trust of their peers, work hard to focus on the things they can control. And they start by learning how to properly manage their emotions.

Train yourself to become a forward-thinker when life pushes you back. Make sure the people on your team are okay instead of adding to the hysterics. Brainstorm ways to identify the positive aspects of each negative situation in order to take just one step forward.

Then, if you’re still pissed, grab a friend, go outside, and unleash hell for a few minutes before getting back to work.

Sebastian Nadal, father of tennis champion Rafa Nadal got it right — “A tennis match has never been won by complaining.”

2. Make friends with people who play on the edges of your sandbox

When I began writing I reached out to one writer a week who was typing words that I liked to read. This alone was a super valuable exercise as it sped up my learning curve a great deal. But the opportunities didn’t begin to flood in until I began to also connect with people who were playing in the same arena but holding a different weapon.

If you want to make it as a marketer, get to know writers.
If you want to be a writer, get to know web designers.
If you want to be a web designer, get to know photographers.
If you want to be more efficient, get to know single moms.

Building a diverse network of people who have different skillsets than you is one of the best ways to minimize career stress while ensuring consistent opportunities are coming in.

The words “I heard about this opportunity and I thought of you!” is the equivalent of career gold.

3. Choose “enlargement” over happiness

During his final installment for his weekly column for The Guardian that ran for over a decade, writer Oliver Burkeman left us with quite possibly the best piece of advice I’ve come across:

“When stumped by a life choice, choose ‘enlargement’ over happiness.”

Many people change jobs to enjoy more security. And don’t get me wrong, there will be times when this needs to be the priority. The other times, however, you’re better off following the lead of Oliver and choosing what enlarges you as a person instead of focusing on what temporarily widens your smile.

Take on projects that stretch you.
Take on clients that intimidate you.
Take on jobs that give you bruises.

You won’t always succeed. But you will learn — which the older I get the more I am beginning to realize is the very definition of career advancement.

4. Focus on honing your “And”

Some people are lucky. They’re born with a burning desire to do something and they have the natural ability that matches their drive. Most mortals, however, need to get creative to stand out. Working on skills that contrast each other to complement each other is a super effective way to make this happen.

The world is full of talented coders.
Strong coding skills “AND” commanding presence on stage is hard to ignore.

The world is full of talented writers.
Inspiring writer “AND” master connector is hard to ignore.

The world is full of talented salespeople.
Persuasive communication skills “AND” super empathetic is hard to ignore.

Make a list of the qualities and skills you possess that other people compliment you on. Then look at how you can merge these qualities together to make a unique pairing.

It’s your “AND” that makes you interesting to others.
It’s your “AND” that also makes you indispensable in your career.

5. Become a master at distilling complicated ideas into simple language

Write down the names of the successful people you know. Without even knowing them, I’d be willing to bet all of them are strong communicators.

But this doesn’t mean they’re all super charismatic. It simply means they’ve done the hard work to learn how to distill complicated ideas and feelings into words the average person can understand.

Investing in a blog will help you to clarify your thoughts while allowing you to gauge whether your message resonated with the masses or not.

Investing in a public speaking seminar will teach you how to tell simple stories that leave a lasting impact.

Investing in an interview coach will teach you how to clearly express yourself and effectively sell yourself.

Warren Buffett got it right — “If you can’t communicate and talk to other people and get across your ideas, you’re giving up your potential.”

6. Live in the space of the next 5 minutes

“They say think big, have a compelling vision. I say think small and do something super cool by the end of the day. Most people see excellence as some grand aspiration. Wrong. Dead wrong. Excellence is the next five minutes or nothing at all. It’s the quality of your next five-minute conversation. It’s the quality of your next email. Forget the long-term. Make the next five minutes rock!”

I wish I had stumbled upon this piece of advice from management legend, Tom Peters, earlier in my career.

I used to beat myself up for not knowing what I wanted to do with my life. But in hindsight, what I should have been doing was focusing on bringing the maximum level of care and commitment into my work no matter what I was doing.

Write the best sentence you can in the next five minutes.
Exercise as hard as you can for the next five minutes.
Give people your full presence for the next five minutes.

Most people think about what lies ahead of them. The future, however, belongs to those who develop the discipline to focus on what’s directly in front of them.

7. Create loads of “White Space” in your day

One of the world’s leading business coaches, Dan Sullivan, has a very simple practice that he claims to be the key to productivity: leave 30 percent of your day unscheduled.

This may sound overly dramatic or downright impossible, but the benefits of carving out time for yourself each day are too big to ignore.

Firstly, prioritizing your free time first forces you to get clear on the tasks that actually move your needle when you are working. Ask yourself: Is social media an effective use of my time? Probably not.

Secondly, you’ll learn how to pace yourself which is key when it comes to long-term success.

Lastly, prioritizing white space first gives you time to get to know yourself and chase your curiosity.

Reserve some time each day to ask yourself better questions.
Carve out some time to reach out to old friends and try to make new ones.
Give yourself time to tinker and explores.

Some people think being busy all the time is a sign of importance. But it’s not. It’s a sign of a lack of clarity.

8. Chase people, not money

As a mentor at various accelerators and learning institutions, I’ve had the pleasure of working with a wide arrange of entrepreneurs and ambitious college grads. Without a doubt, the ones who receive the most attention when starting out are those who focus on chasing advice instead of stressing out about how to make money.

The world is full of talented people. Many of them are incredibly kind and love to do what they can to help others. But these people will never invest in you if you approach them as a way to get rich instead of viewing them as a wealth of potential knowledge.

“If you ask for money, you’ll get advice. But if you ask for advice, you may get money.”

— Advice given to Peter Diamadis by his mentor, Al Furth.

“Who should I be learning from?” is the single most important question you can ask yourself throughout your career.

Positioning yourself as a learner and being curious as hell are seriously attractive qualities.

9. Do what you can — with what you have — to lift up the people around you

For the first part of my career, I was so concerned with what I wanted to do that I rarely lifted up my head to see how I could support the people around me. I regret this. You don’t need to be the most talented person in the world to make an impact. In fact, hundreds of opportunities present themselves to us every day.

Be thoughtful and make the new person feel appreciated on their first day of work.

Be patient and sit down and talk with someone who you can tell is having a bad day.

Be kind and tell the people around you they are talented and you sure are glad they are on your side.

Best-selling author Ryan Holiday got it dead right —

“The fastest way to carve your own path is by helping other people to carve theirs.”

Co-creator of 2 cool boys with an equally cool woman • Career Coach • Business Insider, Fast Co., Forbes • Follow along for career tips and life reminders.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store