The quality of our careers is a direct reflection of the quality of the questions we ask ourselves. 

Billionaire entrepreneur Warren Rustand claims that it takes the average person until the age of 55 to figure out what they want to do with their life. Then, according to Warren, it takes most people ten more years before they finally begin to do something about it.

The good news is, if you can figure out what you want to do with your career, and find the courage to start before the time you retire, you’re ahead of the game. From my experience as a career and communication coach, the fastest way to accomplish this isn’t by searching for better answers, it’s by asking yourself better questions.

You may find some of the questions below basic or even counter-intuitive. However, by thinking about them every day, you’ll not only gain clarity regarding where you’re best served, you’ll also gain the confidence to start to do something about it.


1. Are you opening yourself up to the world?

Opening yourself up to the world is scary. As a guy in the communication world who stutters, I don’t know the extent of your fears, but I feel you. If you are doing something different people will make fun of you. If you are doing something valuable, these critiques will only intensify. As long as human beings continue to be human this will not change.

The next time you are scared to publish an article, count to three and ship it. The next time you are asked to take the stage, grab the mic and give yourself permission to be bad today in order to be better tomorrow.

Both respect and confidence aren’t only gained by getting things right. They are also won by stepping out into the world and trying. You may not attract everyone, but you may attract someone. From my experience, that’s all it takes to get your career moving forward.

Quick but important aside: We don’t get to decide for ourselves what’s good and what isn’t. You may have already created something that will catapult your career. Sit with that thought for a few minutes.


2. Are you heavily involved in your community?

All opportunities have one thing in common: they are presented to us by other people. This means that your primary job is to meet as many people as you can in order to uncover the sweet spot where their needs intersect with your abilities.

Make it a goal each day to make just one new connection. Give some of your time to organizations and causes that you believe in. Join a mastermind group (link piece with BM when goes live) to meet people who are doing what you want to do. Never in the world have there been more opportunities to engage with the world than there are today.

Just don’t forget to get to know people who have different beliefs and interests from you. The world opens up to those who possess an open-mind. Not only that, but Lady Luck doesn’t always come in the form of the people closest to us. Sometimes opportunities come from the strangest of places.


3. What are you doing to improve your communication skills?

Grab a camera, take the dreaded interview question “Tell me about yourself?” and start recording your answer.

Scary right?

The good news is there is an easy way to immediately improve your communication skills: keep recording yourself answering interview questions until you love what you both see and hear. Once you are confident in your abilities to do this step it up a notch by joining a public speaking group in order to get comfortable on stage. We’re talking about 10 hours of uncomfortable practice in each area and your communication skills will be at a higher level than more of your peers.

Imagine walking into every interview and meeting with confidence. Imagine taking the stage and being excited to share your ideas. Imagine being comfortable meeting new people. According to Warren Buffet, “One easy way to become worth 50 percent more than you are now — at least — is to hone your communication skills. If you can’t communicate, it’s like winking at a girl in the dark: Nothing happens.”


4. Are you putting yourself in front of people you admire?

If you take thirty minutes a week to speak with someone who is doing what you want to do, you will never have to worry about your future.

Relationships compound. Knowledge compounds. Experiences compound. Making it a point to speak with just one person a week who holds you to a higher standard than you may even hold yourself takes care of all three of these areas.

Not only that, but this is also another tremendous way to improve your communication skills. To make a strong impression you will have to do your research. To make a connection you will have to listen and ask good follow-up questions. To build a win-win relationship you will have to confidently explain who you are and what you stand for.

The moment you hear the words, “I heard about an interesting opportunity and I thought about you,” from someone you admire is the very moment your career begins to go on the offensive.


5. Are you journaling every day?

The name of every game is pattern recognition. Journaling about not only your thoughts, feelings, and fears, but also your daily interactions with others will bring these patterns to light faster than any other activity.

What went well today? What didn’t? What did I learn? Where can I improve? These questions may sound basic, but in order to reach your goals you don’t need a new recipe, you need healthier ingredients.

It is impossible to have a successful career if you do not have clarity in your vision, certainty in your actions, and a stronghold on your values. Tracking your thoughts, ideas, and experiences will seriously help you to connect the dots you are collecting.


6. What is your unique selling point?

When speaking to podcast host Lewis Howes, relationship expert Matthew Hussey said that the people who keep us awake at night are always more than one-dimensional. In short, people who have successful relationships always have an “And” — ambitious and amazing sense of humor — adventurous and a great listener.

When it comes to our careers the same logic applies. A writer who can also command the stage will always have opportunities. A techie who knows how to sell will always be in demand.

In addition to focusing on your strengths think about which skills can best compliment them. This will not only make your work more interesting, but it will also help you create a profile that is more memorable.


7. Are you saying yes to new opportunities?

Everywhere we turn today we are told about the importance of learning how to say no. Depending on the situation this is great advice. However, nine times out of ten it’s coming from people who already know what they are passionate about. If you do a little digging, you will discover that these same people who shout “If it isn’t a Hell Yes, it’s a No” discovered their passion by eliminating everything they were not passionate about.

We have a life, not a career, and the more experiences you have, the faster you will identify what and who fuels you and what and who doesn’t. Not only that, but most opportunities do not come to us inside our office walls. They come to us by getting out into the world and meeting a new someone and trying a new something. This cannot happen if you aren’t saying yes to situations that make you a little uncomfortable.


8. Did I proactively help someone today?

Our lives are not measured by how many people inspire us, but rather how many people we inspire. The good news is that opportunities to support the people in your community are all around you. The great news is that most people have their heads buried so deep in their phones that they barely take the time to lift up their heads to help the people around them — making it an easy way to stand out.

It doesn’t have to be something big. That young writer who shows promise? Let him know how much you love her work. That new person in the office? Tell them that their efforts are not going unnoticed.

The more you help people to carve their own path, the faster your own path will become clear. Plus, having a reputation for being thoughtful has never hurt someone else’s career.


9. How much do you exercise?

This may sound like an odd place to finish, but Tim Ferriss got it dead right — “If you make your health your number one priority the rest becomes so much easier.”

To win the career you want, you have to bring your energy. To win the career you want, you better bring your focus. To win the career you want, you better bring your positivity. This all becomes much easier if you grab an apple instead of a donut and you do whatever you can to exercise every day.

This doesn’t mean you can’t have some fun. By all means, let loose from time to time. Just remember to do it in moderation. There is much to be gained by being slightly less hungover than your peers.

So there you have it, the 9 questions that lead to a long-lasting, successful career. The good news is the questions aren’t complicated at all. Are you taking steps to improve your communication skills? Are you putting yourself out into the world and trying new things? Are you taking care of yourself and doing what you can to support others?

If you take the time to answer these questions you won’t have to worry about what job to take, you’ll be too busy deciding which opportunity to choose from.