Questions to ask yourself when you are starting out.

Blake Mycoskie
Blake Mycoskie | TOMS
3 min readOct 31, 2016

Good advice is invaluable, but the answers you are searching for are often already inside of you.

Here are a few questions to ask yourself as you start out on your journey.

These questions are inspired by advice from five CEOS of some of the most influential non-profits in the world. It’s evergreen advice that applies to both the public and private sector — or whatever creative community you are entering right now.

What do you already believe in?

One of the most overwhelming parts of getting started is knowing where to begin. But you will be surprised that when you take a look into your life, there are patterns that already exist.

Think about the articles that intrigue you, the books that move you, the leaders that inspire you, the issues that ignite you. Finding your path is not always about carving a new one, but about recognizing the roads you are already adventuring down.

“A mentor asked me, Do you read the New York Times on Sunday? Start keeping a list. What section do read first? Which articles do you read first? Where do you do the most research? And sure enough, a pattern began to emerge.” — Kathy Spahn, CEO, Helen Keller International

What are you awesome at?

We’re saturated with advice on how we can become better. At every age, there is a constant emphasis on what needs improvement. But your twenties are about figuring who you are and what your strengths are. Find a work environment that celebrates your strengths and helps you grow in those areas.

“You know that “work on your weaknesses thing? That’s what you do in school. After school, go to your strengths. What are you awesome at? What do you love? Go do more of that. Because life is short.” — Nancy Lublin, CEO, Crisis Text Line

What are the skills you want to learn?

Instead of worrying about what company you get your first job at, focus on the skills you want to learn. Skills you learn at a small startup will make you that much more valuable when you work at a big company later on. Experience you get in the private sector will transfer over to public sector work down the line. Or vice versa. Make experience your priority, not expertise.

“It’s about getting skills, figuring out what you’re really good and what you love. Get those skills somewhere, learn a lot, learn to understand yourself, and then figure out where to go from there.” — Carolyn Miles, CEO, Save the Children

What world issues do you want to understand?

Oftentimes the first step in solving a problem is taking the time to understand it. In a world with so many complex challenges, there is a pressure to create new solutions. This can be daunting. But there are ways to change the world that require patience to recognize the solutions that already exist. We need innovation, but we also need awareness.

“There is a trend from, ‘Go, go, go, solve the problems,’ to understanding the problems. We probably have solutions for everything. There is a lot of simple stuff we can do — like hand washing and basic education — to promote health in our communities. Instead of thinking of new solutions, let’s think about what we can do with the solutions we already have. I think that’s a good thing, and I hope it gets some momentum.” — Zubaida Bai, CEO, ayzh

What do you have to lose?

You hear it all the time: don’t be afraid to take risks. But the only way you’ll ever be able to fully embrace this advice is when you ask yourself the question, and listen to your own answer.

“I remember thinking in my twenties, gosh if I don’t try it now when will I try it? What I really want to do might not work out, but I have nothing to lose. I looked at risk-taking as an adventure, not something to be afraid of.” — Nancy Aossey, CEO, International Med. Corps

As you continue to grown and learn, make sure to never stop asking questions. Listen closely to the answers — especially your own.

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