380: Chris Winfield: Simple Steps to Work Less and Accomplish More

Chris Winfield is an entrepreneur and productivity expert in New York City. With the use of simple systems, techniques and the power of true focus, Winfield teaches business owners how to get 40 hours of work done in 16.7 and much more.

Favorite Success Quote

“You can’t connect the dots looking forward, you can only connect them looking backward” ~Steve Jobs

Key Points

1. Stop Postponing Your Happiness 

One of the greatest diseases afflicting modern men is something I like to call “postponitis”.

This sickness has ravaged mankind, depriving hard-working men of their happiness, fulfillment, and liveliness for decades. And it all starts with the seemingly innocuous word, “then”.

It goes something like this…

“I am going to work my ass off, make lots of money, then I will be happy.”

“I’ve just got to get this promotion at work, then I will have time to prioritize my health, family, and personal growth.”

“Once my startup hits $100,000/month in recurring revenue, then I can relax and enjoy my life.”

It’s always “then” and never “now“.

Men are living their whole lives in pursuit of some arbitrary goal that somehow gives them permission to live their lives, love themselves, and enjoy their time on this planet.

And frankly, it’s complete bullshit!

Life happens in the now.

It doesn’t happen later. It doesn’t happen when you make your first million. It doesn’t happen when you finally get that promotion. It doesn’t even happen at IPO.

Life happens now.

And if you are constantly living your life in pursuit of something in the future (something that may or may not happen), then you will miss out on life’s most precious moments and end up on your deathbed, wishing that you had a chance to do it all over again.

But you don’t.

You have one life, one shot, one opportunity.

Don’t waste it living for someday.

2. Money is a Magnifying Glass 

Tell me if you have ever heard this phrases before?

“Money is the root of all evil.”

“Rich people are greedy.”

“Money can’t buy happiness.”

If you have been on this planet for any appreciable amount of time, then I’m going to assume that these sayings have been drilled into your head since the womb.

Can I let you in on a little secret?

They’re all a load of crap!

Money is nothing more than a magnifying glass.

If you are a miserable, unhappy, and stingy person, then becoming rich will do nothing except make you a miserable, unhappy, and stingy person with a big bank account.

Conversely, if you are a happy, generous, and loving person, then becoming rich will do little to change your life other than giving you assets that allow you to be more generous, happy, and loving.

Money simply makes you more of what you already are.

So instead of focusing on earning money to attain happiness or believing that money will make you immoral or “greedy”, accept the fact that money is nothing more than a tool that will amplify who you are.

3. Build Your Foundation and the Tower Will Follow 

Most men set out to achieve success in a way that is completely backward.

They start by focusing on their goals instead of themselves.

They are more than willing to hustle and grind on their business for hours on end, but spending an hour in the gym? Not a chance!

They will drop $10,000 on a business consulting package, but spending $2,000 on a new mattress to improve their sleep and energy? Not going to happen!

But here’s the problem…

All of your success, whether it’s in your business, relationships, or social life, stems from one thing. You. 

And if you are not operating at the highest levels, if you are not taking care of yourself, if you are not cultivating habits of excellence, then you are not going to succeed in the other areas of your life (and if you do, then it will not be sustainable).

Therefore, creating a strong foundation of health and high-quality habits is the first step to achieving lasting success.

Start with your body.

Hit the gym at least three times a week, follow a diet that consists of 80% real food (organic if you can afford it), and sleep at least 7 hours a week.

Then, with your body in prime condition start building routines and habits into your life that will expedite your success.

Feed your mind daily, journal, practice gratitude, and recite affirmations.

With these habits in place and your body in an optimized condition, you will be able to achieve your goals at a much faster pace while enjoying your life and feeling fulfilled.

4. The Fastest Way to Recieve is to Give

The best kept “secret” for success that almost every millionaire, billionaire, and wildly successful entrepreneur knows is this:

If you want to receive tremendous value from the marketplace, your relationships, your network, or your career, the first step is to give tremendous value without expecting anything in return.

Let me give you an example from the interview.

Since Chris lives in New York, he has a phenomenal proximity to incredibly powerful and affluent individuals.

And while this might seem like an advantageous situation, you must remember that most successful people get asked for a lot of shit.

They are constantly getting pitched by individuals who are looking for a handout or a handshake and at the end of the day, it can feel exhausting.

Luckily, Chris understood this and decided that he was going to take a different approach.

Instead of hunting these people down and asking for something, he hosts regular dinners and meet-ups where he asks one simple question “How can serve you?”

He doesn’t ask “What can you do for me?” instead, he flips conventional wisdom on its head and offers value for free.

And guess what? It has driven more deals, knowledge, and value to him than any marketing tactic of sales pitch ever has.


Because people love and trust people who are willing to give value.

Just think about this from your perspective.

Imagine you have two friends, one who is constantly asking you for loans, pitching you on his new network marketing products, and pressuring you to join him in business, and one who gives you value in the form of advice, connections, and services… All without expecting anything in return.

Both of your friends are excellent copywriters and you have a client who needs a referral for a six-figure copy contract.

Who would you recommend?

The giver or the taker?

Now ask yourself another question.

How can you give value without expecting anything in return this week? Who can you help? How can you serve others?

As weird as it might sound, the universe has an uncanny way of providing for those who provide for others, so I want to encourage you to be on the lookout for ways that you can bring more value this week.

The results might surprise you.

5. The Enemies of Fulfillment are Ego and Expectation

Since personal fulfillment is a subject that is unique to every individual, I cannot tell you how to achieve fulfillment in your own life.

But I can tell you how to eradicate fulfillment from your life.

Allow your ego to control your actions and your expectations to control your relationships.

Ego and expectation both have their uses, and in moderation, they can be used as effective motivators and filters to ensure success. However, they become problematic whenever you are the slave, not the master in the relationship.

When you allow ego to rule your life and become your sole motivator, you will find yourself pursuing goals that aren’t aligned with your purpose and acting in a manner that is disingenuous and inauthentic.

When you allow your expectations to control your interactions, you will find yourself loathing people that you should love for indiscretions that you shouldn’t have noted.

The more that ego and expectation run your life, the more you will find yourself at the whims of others instead of captaining your own ship.

Learn to curb your ego, swallow your pride and develop some humility.

Give others some breathing room, only set expectations that you yourself can live up to, and be forgiving in the face of failure.

If you do this, I can promise you that you will live a life that is richer, more productive, and ultimately, more fulfilling.

Influential Books

1. The Millionaire Course by Mark Allen

2.The Science of Getting Rich by Wallace D. Wattles

3. Choose Yourself! by James Altucher

4. The Magic of Thinking Big by David J. Schwartz


Connect with Chris Winfield


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