7 Life-Changing Questions to Help You Succeed in 2020 (and Beyond)

In March of 2006, I hired my first business coach, Tom Venuto. 

And during our first coaching session, he asked me a simple question that would change my life in ways I never would have expected.

“Craig,” he said, “What do you want your business to look like in 5 years from now?”

“I want to have a business like Early to Rise”, I responded. 

And that response led me down a path to becoming a better speaker, author, coach, trainer, networker, entrepreneur, and ultimately a better person. 

Yes, Tom’s coaching helped me make millions…

…And yes, his coaching helped me uncover a “cure” for my anxiety. 

But that first question he asked me forced me to declare aloud my dreams and intentions. It got the Universe involved (sounds woo-woo but it isn’t!), pushed me to join masterminds, and got me introduced to Matt Smith (who ultimately introduced me to Mark Ford and allowed me to purchase ETR)

… And if he hadn’t asked that question…

This might not be happening right now.

A good question can change the trajectory of your future and the story of your life. 

As Tony Robbins says, “The quality of your life is a direct reflection of the quality of questions you ask yourself.” 

Realize right now that YOU hold the pen.

And now, it’s time to write down the answers and create the story you want to live.

1. “What were the best/worst experiences of 2019? What do I want more or less of in 2020?” 

It’s easy to set big goals. But all too often, we let our peers, competitors, and the media push us into setting big goals that aren’t in integrity with what we truly want. 

We allow comparison to seduce us into a lifestyle that is inauthentic and out of alignment with our true values and vision. 

So today, with 2019 in the rearview mirror, I challenge you to look back on the year objectively to discover the experiences, relationships, and pursuits that really fulfilled you. 

What were the things that happened in 2019 that set your soul on fire? What experiences do you want more of in 2020? And, most importantly, what is really required to achieve them? 

For example, let’s say that last year you prioritized family time more than ever before. You took epic vacations, you made it to your kid’s sporting events, and connected more deeply with your spouse. And the result was a feeling of intimacy, closeness, and fulfillment that far outweighed your professional achievements. 

By recognizing this, you can strategically plan for even more quality time and adventures with your family in 2020…even if they come at the expense of making more money. 

Now, take another mental step back…

What were your worst experiences of 2019? And how can you reduce them in 2020, or eliminate them altogether?

For example, maybe you agreed to a lucrative business project that added an extra 20 hours of work to your plate each week. 

When you think back on it, you realize that the money you earned from that project paled in comparison to the stress, anxiety, and overwhelm you felt completing it. Knowing this, you can set stricter boundaries in 2020 around the types of projects you will and will not pursue. 

Or, if you traveled too much and spent too many weeks away from home, set strict rules about the types of engagements you will and will not travel for. 

For example, maybe you worked way too much on menial tasks. Plan to outsource the work that doesn’t require your specific skillset. 

By simply taking the time to pause and reflect on your year, you’ll gain a more objective understanding of what really matters and prioritize your time in 2020 accordingly. 

2. “If I had to achieve my ten-year goals in the next six months, how would I do it?”

Peter Thiel asks this question, made famous by Tim Ferriss’s book The Tools of Titans, of every Founder and CEO who comes to him for funding. 

But here’s the interesting part. 

Peter doesn’t expect the companies in question to actually accomplish their 10-year goals in six months. Instead, this thought experiment is designed to force them to challenge their assumptions, identify the inefficiencies, and think 10X bigger than they are today. 

Right now, I challenge you to answer this question. 

If you HAD to hit your 10-year goals in the next 6 months, gun to your head, how would you do it? 

What strategies would you need to change? What would you need to STOP doing? Who would you need on your team? Who would YOU need to become? 

Maybe you’re easily distracted by your Instagram feed or email notifications or a chatty coworker and you need better boundaries to protect your time and attention. 

Maybe you’re working your fingers to the bone on menial tasks and unnecessary errands and you need to hire a new team member to outsource the busy work and give you the space you need to work inside of your “Area of genius”. 

To help you solidify your answers to this question, I’ve developed a simple tool I use with all of my $25k/day coaching clients called “The Billionaire Time Matrix.” 

If you’ve never completed this exercise before, pull out a blank sheet of paper and a pen and take 10-minutes to complete this. 

Draw a box with four quadrants, and write these questions in each of the quadrants.

What do I hate doing?

What is NOT my job?

What should I stop doing?

What are my distractions?

Be brutally honest with yourself here and leave nothing out.

Once you’re done with this exercise, analyze the items on this list and identify the #1 action step you must take today to get closer to your ultimate vision. 

Once you’ve successfully delegated, eliminated, or automated all the things that are killing your time, you’ll have freed up 10-15 hours each week and brought yourself 10X closer to hitting your big goals. 

3. “If money were no object, how would I spend my time? What would I do differently than I’m doing right now?”

All too often, we defer doing the things we really want to do until we hit a certain level of financial success. 

But here’s the thing… 

Most of the things you REALLY want to do (spend more time with family/friends, travel more, learn a new language, instrument, etc.) are all readily available NOW, regardless of your financial level. 

So ask yourself… What are a few things you’ve been delaying until you hit that magic number? What are the things you would do if money weren’t a concern?

The next step is simple. 

Prioritize those things in 2020. 

Stop putting off the things you want until you can “find” the time. Make the time. 

The more energy you pour into yourself…your hobbies, passions, and relationships…the more energy you have to pour into your professional and financial ambitions. 

Don’t believe the hype that the most successful people in the world grind 24/7. They don’t. 

The legendary Magic Johnson spends weekends at his house in Laguna Beach and travels to Europe every year. My friend Bedros Keullian never misses date night with his wife. Jack Dorsey dedicates each Saturday to unplugging from his devices and hiking.

Identify the hobbies and activities that restore your soul and do more of them.  

Every area of your life will be better when you do. 

4. “What problems am I facing in my life that I can spend money to solve?” 

There’s an old saying, “What got you here won’t get you there.” 

And it’s true. 

What gets most entrepreneurs to the “promised land” of 6 or 7-figure success is simple. They work hard for long hours every single day. 

And for a while, this winning strategy works. But once you reach a certain level of success, you’ll find that this winning strategy is the reason you’re starting to lose. 

Because the simple truth is that you can’t do it all alone. And more importantly…there’s no reason to. You don’t need to suffer in silence and break your back every day to hit your big goals. 

So ask yourself…what are the problems in your life that you can spend money to solve? 

Who or what do you need in your corner to simplify your life and eliminate problems? 

Are you working too many hours? Buyback your time by hiring an assistant or a commission-based sales rep to free up your schedule.

Are you struggling with your weight and energy level? Invest in a personal trainer or meal delivery service. 

Are you unable to keep your house organized? Spend $100 a week to hire a housekeeper. 

Do you waste hours each week waiting for software or websites to load? Fork out $2,000 to upgrade your laptop and router. 

You get the picture. 

Money doesn’t solve everything, but it solves a lot of things. 

And in my experience, the money I spend to buy back my time is always an investment that yields disproportionate results in the long run. 

5. “What if nothing was wrong?”

It’s easy to look at other people’s success and imagine that, because we aren’t at their level, we’re doing something wrong. 

But what if everything was exactly as it was supposed to be? What if there isn’t anything wrong with where you are right now, and you simply need to be patient, trust the process, and continue investing in yourself and your growth? 

Listen… 

There is always room for improvement. And no matter how many proverbial peaks you reach or how much success you achieve, there will always be things in your life with which you are dissatisfied. 

But catastrophizing this room for improvement (e.g. “I’m only exercising 3 days a week instead of 5…I’m such a lazy horrible person!) does nothing to move the needle forward in your life. 

The truth is you have more than 99.99% of human beings that have ever existed. You have a roof over your head, food on the table, and at least one person who loves you. 

And the fact that you aren’t where you want to be (which is a target that is always out of reach) doesn’t mean there’s some fatal flaw with who you are as a person. 

So take a deep break and relax. Everything is going to be ok and the problems you are facing are likely much less serious than you imagine. 

6. “What activities and obligations account for 80% of my stress? How can I eliminate them to increase my performance and happiness in the New Year?” 

Most entrepreneurs I know could eliminate 90% of their stress, anxiety, and overwhelm by making 2-3 small shifts in their life and business. 

Firing on bad client or crappy employee. Paying someone else to write the articles and emails that eat up an entire day of productive time. Eliminating the most frustrating service from their offer. Setting boundaries around a toxic family relationship that leaves you feeling drained and exhausted. 

Ask yourself right now… 

What are the 2-3 things in my life or business that cause 80% (or more) of my stress and anxiety? 

And how can you eliminate (or significantly reduce) them in 2020? 

Even if it means losing money in the short term, never underestimate the hidden cost of chronic stress and anxiety. 

Sure, you might lose $3,000 in monthly revenue by firing the client who takes up too much of your time and makes unreasonable demands from you and your company. But the peace of mind and extra time are worth the cost. 

Yes, it might be uncomfortable to fire the underperforming employee who’s been with your organization for five years…but doing so will reduce your stress and give your ex-employee the opportunity to find a position for which they’re better suited. 

Realize that the world we live in is abundant. There are more opportunities and options than ever before and there’s no need to suffer through months or years of unnecessary stress and anxiety. 

And it’s only by eliminating the bad and even the “good” that you open up room in your life for the “great.” 

7. “What really matters during this season of my life?” 

A few years ago, I spoke to a large group at an Entrepreneurship Camp in Lithuania about the importance of creating a vivid vision for your life. After the session, I chatted with a young man named Steve.

He wanted to do it all. He wanted to exercise, he wanted to write, and he wanted to spend time with his girlfriend. He asked me a question many of you have likely posed to yourself: “How do I know what to focus on in life?”

The truth is the same for Steve as it is for you…You’ve got to figure out your season of life and give all you’ve got to that area.

Maybe you’re in the season where you’ve had success with your business, your kids are grown, and now, it’s time to shift your priorities to focus on recovery and improving your health. 

Or if you’ve got young kids at home, it’s the season to focus on them as much as possible, making sure you get work done in time to be home for dance recitals or basketball games. During this season, you’ve got to be sure you aren’t wearing yourself thin so that you can be at your best when you’re with your family.

You might be in the season of life where you’re young, unencumbered, and don’t have as many obligations in your personal life. As such, you can give more time, energy, and attention to building wealth, knowing that it will one day serve as the foundation upon which your family and dream life will be built. 

Whatever season you’re in, you must gain clarity on your values and vision and determine what’s truly important right now. 

By doing so, you will simplify your decision making, gain clarity on your goals, and start taking the right actions to get you where you want to be. 

Happy New Year!