âIt is impossible to live without failing at something, unless you live so cautiously that you might as well have not lived at all, in which case you have failed by default.â
J. K. Rowling
Quick announcement before we get into this post. To help people absolutely crush 2020, Iâm very excited to announce The Day Won Mastermind! This begins on 24th February 2020 and will be a 3-month program. Itâs designed for professionals and entrepreneurs who want to find their voice, build their tribe, and make an impact.
I want to make sure I can allocate the proper amount of time for each person, so spots are strictly limited! I'll be sharing everything I know about success, happiness, and creating a life of freedom. If you want the ultimate foundation for success in 2020, to have me work with you on your business and your personal life, and to surround yourself with people who can help you along the way, grab one of the places while you can.
There's also a special bonus for the first 10 people to join. To reserve your place, or get more info, go to The Day Won Mastermind.
Alright, back to our post!
What does the "New Year" mean to you? For most people, it's a night of partying or a chance to have a holiday. Both of those are fine because it's important to have fun, but it's useful to know that the New Year marks a complete orbiting of the Earth around the sun. Recently, more and more, I've enjoyed it as an opportunity to refocus on what's most important and chart a detailed course for the next 12 months.
This celestial significance of the New Year gives us three insights:
- Change is inevitable. Everything is constantly changing.
- Our time is running out. We don't know how many orbits we'll be here for, so we need to make the most of them. Recent tragedies with the Australian bushfires and the passing of basketball icon Kobe Bryant give us more confronting reminders.
- We should worry less about what others think. As comedian Joe Rogan said, "If you ever start taking things too seriously, just remember that we are talking monkeys on an organic spaceship flying through the universe.â
As we begin our list, grab a notepad and brainstorm how you can apply these into your life. If you can do that consistently, your success in 2020 is assured.

1. Clearly define goals.
Napoleon Hill wrote that the starting point of ALL achievement is desire. In fact, he made it the very first principle of Think and Grow Rich, so that gives you an idea of just how important this step is. After all, if you donât know what your perfect destination looks like, how can you expect to end up anywhere near there?
Once youâve got that perfect destination in mindâin each area of your life thatâs important to you (download this free Success Plan Template for a step-by-step guide)âturn it into clearly defined goals that are:
- Emotionally-charged, and
- Unique to you.
As youâre preparing these goals, let your thoughts run wild, unencumbered by what others may think. On this journey to living a life on your own terms, youâre going to encounter a lot of people with their ill-informed opinions, but you must remember that the most important opinion is how you feel about yourself.
Financial freedom in particular is a huge goal for so many people, as it should be; therefore, I strongly encourage you to read this post 'How to Become a Financial Winner' to get yourself on the right track. A recent study even revealed that wealthy people live longer and in better physical health, so make it a priority for you.

2. Hang out with the right people.
Ever driven in a Ford car? Iâm sure you have. You might even have owned one. In the 109 years since it was founded, the Ford Motor Company has built more than 350 million automobiles, averaging a new car sold every 10 seconds. Its founder, Henry Ford, passed away in 1947 with a net worth of more than US $200 billion (adjusted for inflation).
Not bad for a poor, illiterate kid.
Henry Ford once said: âMy best friend is the one who brings out the best in me.â Thatâs one of my favorite quotes because seeing how your life has changed as a result of someone elseâs presence is a very clear yardstick for the value of that relationship.
Often, we feel obligated to keep associating with people just because we went to school with them, or theyâre a family friend, or maybe even a family member. But itâs important to protect your energy source, which includes understanding the following:
- You need to associate with those who have a common FUTURE (not a common past).
- You canât hang around negative people and expect a positive outcome.
- Toxic people are still toxic, even if theyâre disguised as family.
Over the holiday period, you mightâve bumped into some of the toxic people that made your skin crawl. Well, now is the time to replace them with someone who makes you happy and helps you succeed!
If youâre not sure where to start, join the Win the Day Facebook group and introduce yourself! Weâve got almost 400 people there just looking for ways to help others.

3. Create a positive environment.
A big learning for me in the last few years is recognizing the full magnitude that our mental state has to the meaning we attach to a given situation. If weâre in a grumpy mood, weâre going to focus a lot more negatively about any situation presented to us; yet, if weâre in an inspired mood, weâll see the BEST in any situation.
There are mental tricks we can play to get into a positive mood, just as there are things that pull us into a negative state. What can you do? Just as we think about intent for how to structure the day, we can apply this just as readily to environmental care:
- Remove clutter from where you live/work. To do this, ask yourself if an item sparks joy; if it doesnât, get rid of it. Simple.
- Eliminate items that distract you or cause you to procrastinate.
- Surround yourself with inspiration. If youâve seen the Win the Day show on YouTube, youâll have noticed the enormous canvas print I have in my office that says âACTION: The difference between wanting and having.â
Even listening to a podcast or an audiobook once a day can help you give the constant repetition of positive materials to put you in the right head space.

4. Have strong systems to achieve.
This is where most well-intentioned people fall down. The absolutely essential next step after defining your goals is to BUILD them into your daily life so you know, every single day, what work you need to do and how it relates to your long-term mission.
Every year, I complete the Success Plan Template, then turn those 90-day goals into action items that then go into my calendar. After 90 days, I have another notification that goes off to do the next 90 days worth of goals and action items. What that is release yourself of stress today because you know the outcome already.
Contrast this to those who either donât set goals in the first place, or doâbut never create a strong system to actually achieve them.
Thereâs one final fail-safe measure here that you can take: When you wake up each day, write down three things youâre grateful for and three things that would make today a win. This ensures that EVERYTHING you do is with intent and positions you as the hero of your own story, rather than having to stare glumly or enviously at what everyone else is doing.

5. Attach happiness to the present.
The digital age has greatly exacerbated our self-esteem. When we donât have a worthy method for self-evaluation, we look elsewhere for it, and images of âperfectâ people are thrust into our vision from all the social media platforms. This is where phrases like âIâll be happy ifâŚâ and âIâll be happy whenâŚâ become our mantra, as we attach our happiness to the success we believe others have that continues to elude us. This can be anything, from a desirable partner to a thriving business, or even having someone elseâs body.
But true happiness is not just found in the present, itâs found by being present. So enjoy being in the present, come rain, hail or shine, and say âYes!â to life more often. Just be aware that this step will be much easier to complete after youâve done the preceding four steps.

6. Join a mastermind.
Rather than spending tens of thousands of dollars and years of your time trying to figure it out yourself, find someone who has the success you want and do what they tell you! If you join a mastermind that gives you unprecedented access with someone you admire, while allowing you to collaborate with other like-minded people, your idea of what you can achieve will increase exponentially and your journey to getting there will be so much faster.
To find a good mastermind, just make sure:
- The person is the real deal. If they list publications that theyâve been featured in, or achievements theyâve had, make sure you can verify it.
- They stand behind their own products. If they donât allow you to try it for a decent amount of time, and then get a complete money-back guarantee if the program is not working for you, itâs not worth doing.
A good mastermind will give you massive amounts of structure, challenge, and accountability in all areas of your life.
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I wish you every success and happiness in 2020!
Onwards and upwards always,
James Whittaker
PS - Remember to secure your place in The Day Won Mastermind (or schedule a call to find out if it's the right fit for you).