How to Win

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The biggest mistake people make when trying to change their life is chasing the “big win”. We love the idea of doubling our money overnight, of losing 20 pounds in one week, of starting a successful business in under a month. The faster the better. But these big wins are often unrealistic and only lead to one outcome: short-term failure. 

Chasing big wins causes us to lose our long-term focus and often leads to poor decisions in the short-term. The solution to overcoming that job you hate is not to walk into the office tomorrow, tell off your boss, and declare yourself free from the man. It won’t work. You’ll be working at McDonald’s in less than a month just to pay your bills.

The way to win is not by making a bold declaration in a moment of motivation that you vow to “start grinding” or “putting in work”. That never works. It’s not about posting on Facebook about how you’re making a drastic change. It’s not about New Years Resolutions. 

No, in order to win you must do the exact opposite of all these things. Don’t announce your goals to anyone. Don’t rally your friends for support or start a group message with everyone you know to share your big, audacious goal. Don’t tweet, post photos, post videos, or write inspirational posts on social media to get attention for your goal.

Instead, chase the small wins. 

Don’t vow to meditate for 30 minutes every morning before work after reading an inspirational post on how meditation will change transform your life. Instead, take a few deep breaths in your kitchen before your leave. Then again the next morning. And the next.

Don’t send out a mass email to all your friends telling them about a new business you’re starting. Instead, spend that time finding a domain and hosting plan to start building your website online.

Don’t go delete your Netflix account tonight after reading some article about how TV is preventing you from being the person you want to be (although it probably is). Instead, spend 30 minutes reading tonight instead. Then again the next night.

Don’t toss out all the ice cream in your freezer in a brief moment of discipline and post on Facebook about how you’re no longer eating sweets. Instead, just skip out on desert. Just for tonight.

Don’t go buy a new closet of workout clothes. Just go to the gym today.

Don’t declare yourself a minimalist and throw out all your kids toys while they’re at school. Instead, let them choose one of their toys to donate to a children’s shelter when they come home.

Don’t start trading penny stocks and hope to hit it big this week. Instead, open up an IRA today and invest in an index fund.

These are all ways you can win small. Not only is winning small less stressful and more realistic, but it has a curious side-effect: it helps us gain momentum. Convincing your kids to throw out all their toys could be challenging. But donating one toy? That’s a small step in the right direction. It makes it easier to donate another toy. 

Our society has a love affair with “big wins”. We buy products that promise to change our lives not only dramatically, but instantly. We have social media platforms that are begging us to share our biggest dreams and aspirations with our followers, even though this doesn’t help us get any closer to achieving these dreams. We praise the idea of “overnight success”. We glorify the big wins.

But the truth is, big wins don’t exist. A big win is simply a pile of little wins accumulated over time. The most surefire path to becoming a millionaire is to practice diligent saving for many years. The best way to lose weight is to choose salad over desert one day at a time. The most effective way to radically change your life is not to make a big announcement, take drastic action today, and hope for success to show up tomorrow. Instead, chase the small wins and let them accumulate into big wins over time.


I strongly suggest using free financial tools like Personal Capital to track your net worth, spending habits, and cash flow to help keep an eye on your money. The more you track your finances, the better you get at growing your wealth!

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8 Replies to “How to Win”

  1. “But donating one toy?” I don’t know but my son made a little pile of toys in his room and woke up one morning and said I want to donate those. I felt so proud of him. Of course he’s a kid and I later found out that my wife said he can get new stuff only if he gets rid of his old toys, :-). I’m trying to cut down on my own material things but at the same time applying very gentle pressure on my family to do the same and the internal fullness it will create as a result.

    1. Haha that’s a funny story, at least he has experienced what it’s like to let go of things! I think you’re using a great technique by slowly encouraging your family to place less importance on material things. The more we let go, the more we realize that it really is possible to live with less stuff without feeling deprived.

  2. Great Article Zack! I am always amazed about how people react to vegetarians with “I could never go without eating meat.” I talked to a friend, who has been a vegetarian the majority of her life, and she said that it is just something she happened to do over time. She talked about it like it was an accident. Over the course of months/years, she cut out a few meat foods. She said one of the last things she removed from her diet was actually salmon.
    I thought this was a cool idea of switching over slowly instead of all at once. It’s a similar idea as chasing small wins. Eat a vegetarian meal here or there, instead of proclaiming your righteous veganism all over the internet for the two days you do it. Thanks for writing this high-quality article!

  3. I have gotten a lot better at this subject but chasing the big win is still alluring.

    I have a tendency to jump into hobbies and spend more than I should. I bough workout clothes after two or three days of working out and then that fizzled out. I bought expensive tools when I wanted to woodwork only to have a bunch of fancy unused tools. In starting a blog I spent on multiple themes in hopes of going viral.

    I have learned now to take every day and try to capture a daily win. I have been able to take a deep breath and enjoy things more without focusing on the big win. Great post as always!

    1. I like the term “daily win”, I think that really captures the whole idea here. It’s not about becoming a superstar overnight, it’s about doing what we need to do day in and day out to score those “daily wins”. In the long run, this is ultimately what separates the winners from the losers. The part that most people struggle with is simply lack of patience. Are we willing to patiently acquire the daily wins or are we chasing the elusive big win?

      Thanks for the feedback 🙂

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