Ask Yourself These 4 Questions To Be More Successful

What’s the first thing that comes to mind when you hear the word “success”? For many, it’s the quintessential American dream: big house, nice car, six-figure pay check. But as the world and society evolves, so does the definition of what it means to be successful. 

While the picture of success is subjective, it can be a challenge to identify your own version of it. But it doesn’t come to those who wait — it comes to those who are willing to put in the work to make their dreams for the future happen.

Do you want this year to be your best yet? Ask yourself these 4 simple but powerful questions, and get yourself on the right track. 

1. What Does Success Look Like For Me?

I’m part of a business program at MIT called The Birthing of Giants, where I was fortunate enough to meet Paul Orfalea. Paul is the founder of Kinkos, the go-to place for printing and copying from back in the day, that sold to FedEx for a cool $2.4 billion. I was fascinated by Paul’s answer to the question, “What is success? He said, “That’s simple. If my kids want to hang out with me when they are adults, that’s success.”

Think beyond the money and envision the life you want to be living. Do you want to work a 9-to-5 or do you want to set your own schedule? Do you want to pick your kids up from school every day? Do you want a week’s vacation or do you want the freedom to take a dream trip every year? Imagine the kind of success that you can look back at as a 90-year-old, and think “yes, I lead a successful life.” Now make that basis for every decision you make from here on out. 

2. If Money Was No Object, What Would I Do?

Everyone has played the lottery game, where you imagine what you’d do if you hit the jackpot. Maybe you’d travel around the world, buy a boat, or be practical and invest. Now apply that thinking to your career: if you had all the money in the world, what would you still choose to do with your time?

If you love helping people, maybe you should pursue a career that allows you to do that. If your passion is leading teams, consider becoming a project manager or starting your own business. All too often, people let ego and money get in the way of following their dreams. So get curious, and find that magical intersection between your skills and your passions. Maybe there’s a career opportunity just waiting to be discovered!

3. What’s One Thing That’s Been Holding Me Back? (And How Can I Finally Let It Go?)

When it comes to achieving your goals, are you your own worst enemy? It’s pretty common to let fear of failure or self-doubt stand in the way of living the life you want. Look back to the past few years and identify one area where you’ve been putting up your own roadblocks. 

If you were rejected at your last job interview, it can be terrifying to put yourself back out there – so maybe you’re settling for a job you don’t like instead of trying again. If you twisted your ankle the last time you went skiing, it’s natural to avoid getting back out on the slopes. But negative thinking can be debilitating and won’t help you create your dream life. Instead of allowing your past failures to limit you, learn from them and use them as a tool for growth.

4. What Is My Guiding North Star?

As a successful business owner, wealth was definitely my driving force in my twenties. But when I was offered $100M to sell my business, I realized something. Sure, the money part is nice, and I’m very privileged — but what truly brings me joy is the journey, not the destination. 

Imagine if there was one photo that could capture what living the dream means to you. What would it look like? Where would you be and who would be with you? Crystallize that snapshot in your head, then start to figure out what it will take for you to get there. 

Yes, building wealth will likely be a part of that… but for what reason? Very few people, if any, will say that photo shows them standing by a stack of money. What are you working towards? What is it all for?

While these questions are a jumping-off point to inspire some big success for your year ahead, their true power comes from how you follow through.

Once you’ve taken the time to think about and answer each one, make sure you check back in throughout the year to hold yourself accountable.

It’s a powerful exercise to determine what truly makes you happy — and happiness, after all, is the true definition of success.