Life Coach Amy Steindler, founder, InsightOut Life

Who she is: When it comes to achieving the life you are dreaming of, no one is better at helping you get on track than a life coach. Amy Steindler is a case in point.

What she does: Amy’s Annapolis company, InsightOut Life, is helping dozens of professionals get on track so they can have the lives they have only dreamed of—but were afraid to seize.

Why she does it: “After working through my own career transition, I started noticing how many others felt confined to jobs or relationships because they knew on some level that it was wrong for them,” Amy says. “I realized that I had finally arrived at that proverbial intersection of what the world needed and what I had to offer. The timing couldn’t have been better, and my mentor, Martha Beck, helped me find my own mission—some sort of cosmic recruitment, pulling people into their right lives, helping them find their way, helping to mend them, and by extension, the world.”

Living the Life You Deserve

By Hope Katz Gibbs
Truly Amazing Women

What does it mean to live the life you deserve? It’s a tough concept to contemplate for many 21st century “human doings,” who were brought up to believe that if we followed the rules, got As and worked our hearts out, that we’d meet with success—or at least some semblance of it.

Then life happened. Careers, bosses, bad economies, missed opportunities, husbands, kids. Some good. Some not so much. And at every turn, there we were—wondering if this is the best we can do, the most we can have.

Sure, “it’s all good,” but in those moments when we’re just not sure that it actually is, when we’re down on our knees in a puddle of “caterpillar goo,” it’s good to know there is a guiding light like Amy Steindler.

We talked to her about how she came to become a life coach, how she sets goals, and how she helps others set and stick to theirs.

Hope Gibbs: I understand that you came to Insight Coaching after 29 years in sales and management, working for big corporations and a Wall Street firm whose names we would recognize.

Amy Steindler: That’s right. I was successful no matter what I did, which was a blessing AND a curse, making it harder to uncover what I really, truly, LOVED to do. I stumbled into my sales career without much consideration, going from job to job without a plan. Over time, I realized that my “career” felt hollow, but I had no idea what else to do.

In 2008, I took three of my four weeks of vacation all at once to see if time and distance would give me some perspective. After 17 days of quiet bliss, rafting the Colorado River through the Grand Canyon in October, I emerged somewhat changed. Everything looked different. Little did I know that I had returned to a completely changed world.

Hope Gibbs: Let me guess.

Amy Steindler: Yes, the market had fallen off a cliff that made the Grand Canyon look like a crack in the sidewalk. I went back to work, and was truly, madly, deeply miserable. I began to question why I was spending precious days stressed and unhappy. Once I noticed what I was feeling, I had an epiphany: I wasn’t living authentically, I was going through the motions to bring home a comfortable paycheck. So I set some new goals for myself.

Hope Gibbs: Tell us about the process. It must have been difficult.

Amy Steindler: It was difficult, but I knew I wanted to choose a life that allowed me to express my creativity and my true nature. I left my job in the worst economy since the Depression to honor a longtime dream to spend a month snowboarding. It was the first time I ever really allowed myself to fulfill a dream, and it felt amazing. But when the month was up, I was at a loss. I wanted that amazing dream-fulfillment feeling to be part of my day-to-day life, but I had no idea how to have that.

I interviewed with other financial firms, just to make sure I wasn’t throwing away the career of a lifetime. As you can imagine, it still didn’t feel good. It was a confusing and disorienting time, and I had no idea how to proceed. What I really needed to do was to allow myself time to dream about the things I loved to do.

That’s when I discovered the work of Martha Beck, whom you may know as a columnist for O, The Oprah Magazine, and the author of several books, including “Finding Your Own North Star.”

I learned how to let go of my old beliefs about who I was supposed to be, and focused on my unique gift, which turned out to be life coaching. I set a goal to get my life-coaching certification, and here we are.

Hope Gibbs: Tell us more about your practice. How do you help your clients set goals, or do you take another approach to helping them find the life they yearn for?

Amy Steindler: The most important thing about setting goals is to make sure you’re ridiculously excited about achieving them. Question any goal that doesn’t feel absolutely delicious, and be aware of your body’s reaction. If it makes your heart want to fly out of your chest on wings when you think about it, it’s the right goal for you.

If you feel the distinct sensation of wearing shackles, and a pit of dread in your stomach, rethink it. My clients know that you can’t set goals until you truly understand and embrace your life’s purpose, which is deeply challenging and highly rewarding work, and often is what has led them to seek my help. After that, goal setting is a joyful process, rather than drudgery.

Hope Gibbs: How has this new life changed your perspective on goal setting?

Amy Steindler: I no longer set goals that I think I’m supposed to achieve, but focus only on those that come from my essential self—that tiny, internal wise person who knows what’s best for me. I can’t become an expert in something unless I’m so interested in doing it that I lose track of time. That’s one way to know—without a doubt—that you are on your true path.

Hope Gibbs: Can you give us an example of the goals you are setting for 2012?

Amy Steindler: I’m wildly excited about combining life coaching with other creative disciplines to give clients multiple opportunities to discover and embrace their essential selves. I’m creating another Through Your Own Lens retreat, which uses photography as a tool for self-exploration.

I am also thrilled to be working with a ceramic artist to create a workshop where we use clay to give physical form to how our fears hold us back. I’ve got a couple of extremely fun workshops coming up in February and March that use snowboarding as the doorway to unlock new insights about how the riders live their lives. I could go on, but I might burst into flames.

Hope Gibbs: We could talk all day, I’m sure, but to finish up, can you share some thoughts on goals that you are hearing your clients set for 2012? Is there any pattern or trend that you are picking up on?

Amy Steindler: My business clients want to build their businesses while remaining true to their authentic selves, and it’s difficult for them to make the leap of faith that requires them to let go of the fears that drive them to take on work, or clients, that they don’t have a crazy, joyful passion for.

Their goal-setting is focused on allowing themselves to set boundaries for their businesses that help attract clients who appreciate their work, and pay them on time. My individual clients face fears about leaving “secure” soul-sucking jobs and speaking out clearly about what they really love to do.

It’s hard for them to believe that everyone has the ability to do what they love, AND make a living at it. It’s my job to help them see exactly how that’s possible. Their goals are about letting their light shine, trusting themselves, and enjoying the process.

For more information, visit Amy’s website at