Lynan Saperstein’s path to becoming CEO of The Big Factor, which guides aspiring entrepreneurs toward realizing their goals, was a winding one. Over the course of her career, she tried on several roles—EMT, social worker, nanny—before becoming a coach and mentor who helps to transform people’s ideas into concrete, thriving businesses. One of The Big Factor’s major projects, helmed by Lynan, is the Trailblazers Retreat, a week-long session which melds business and adventure.

This May, Lynan tapped into her identity as an Explorer + Spiritual + Visionary by bringing together a group of executives, freelancers and creatives to the seaside town of Spilt, Croatia. There, with the support of Lynan and several workshop leaders, they developed plans to make their businesses and projects flourish. We spoke to Lynan about her journey toward becoming a leader and guide, and about how to turn an innovative concept into a trailblazing reality.

Were you surprised at all by your archetypes quiz results?

It was surprising—it was cool that taking a quiz gives you all that information. Those three types are so me. Explorer coming first made a lot of sense: I’m a traveler, and I’m an adventurer—that’s a huge part of who I am and why I started the Trailblazers retreat. I love doing something no one else has done before.

Tell me more about how your archetypes inform the work you’re doing now.

Spirituality is a huge part of my lifestyle. I think it’s how I make decisions, and what makes me feel drawn to particular people. It’s probably my guiding force, and helps me determine whether something feels in alignment with who I am or not. It’s how I make my decisions. As for being a Visionary, I think that’s a huge part of my personality and my brand. People know I’m always dreaming up some crazy new idea or some trip or project for my clients. I’m often that person who is thinking of things before the greater population is, and a lot of the people I work with and collaborate with and hire me are like that as well. They’re seeing things before they exist. 

You tried on many different roles before founding The Big Factor. How did you find your way to coaching?

I find that people who become entrepreneurs often have tried a lot of different jobs, but none ever quite felt like a 100% fit. I’ve always felt hungry for life, and am often looking for new experiences, so for me, my career was a place to play. At one point, my corporate job imploded and I hit rock bottom. I thought, “I have a clean slate, what do I want to do?” Which is when my Spiritual side got activated. 

I started going to a reiki meditation circle in Midtown Manhattan, and met the coolest people and started working for the woman who ran the center. I found that leading workshops was what I had always wanted to do. My first step was doing a coaching training. I had done coaching as a social worker, and I was a psych major in college, so it flowed naturally. And the more I did it, the more I loved it. I found my groove. 

What are the skills that make an effective coach? I would think your background in psych comes in handy.

A desire to help others, and being a super empathetic person is very important. Being able to put yourself in someone else’s shoes. Being able to not talk at someone, but instead just be present with them, meeting them where they’re at. That’s where my social work training comes in. The other piece is just experience. There are coaches out there who are new to the field, but life experience is really the most powerful tool a coach can have. Can you talk to a person? Can you inspire confidence in them? A good coach is someone who is confident in him or herself. 

Tell me about who your clients are—what kinds of industries do they come from? Where are they in their careers, and what are their goals?

I work with people who have an entrepreneurial spirit, or who have a business that’s doing okay, but they have bigger dreams for it. They want to create an impact and have a legacy. They have that passion and drive and ambition. For example, I might have a client who is still in a corporate jobs and wants to, say, be a personal trainer, but maybe he’s a banker and it’s hard for him to let go of banking. We set up his business and his web presence, so that when he leaves his corporate job he can make as much money as he was in banking, but now with his side business. We market, write strategies, and develop implementation plans.

How did you come up with the idea for the Trailblazers retreat? Who do you think can most benefit from it?

Last year I worked with three clients on sites in Costa Rica, Peru, Italy and Chile. When I was in Costa Rica, I worked for a yoga retreat and lived there for a month and a half. My client suggested I have my own retreat—he kind of gave me a challenge. So I started visualizing it and creating some space for it, thinking about what it would look like, who would be there. The word “trailblazer” came to my mind—I thought of people who are pushing the edges. It can be lonely to be where no one has gone before. So I like to say I somewhat selfishly created the retreat, to bring my tribe all into one space. I bring in the most expert workshop leaders I know, and we’ve had amazing results. You can just come in with a side gig that you want to make your life, and plug into this community, and leave and feel, “I can do this.”

What advice would you give to people who would like to become entrepreneurs and start their own businesses?

There are three things I would say. The first is to get really clear on your vision. Ask yourself if you want an online store, a brick and mortar store, private clients, corporate clients. What is it that you want? Do you want to be a personality, the next Oprah or Martha Stewart? 

The second step is to start talking about it with everyone you meet. It’s a vision at first, but the dream becomes a reality when you start speaking about it and it becomes a part of your daily life. Tell it to anyone who will listen. You never know what opportunities will show up. I had a client who was at a farmers market and she was talking about her business. A man behind her buying tomatoes overheard and became an investor, and ended up giving her $20,000. You never know the connections that will show up. It’s about calling in what you want.

The third piece is, you’re going have to do some hard work. Being an entrepreneur is not easy. Make sure you’re doing something you’re passionate and driven about, something you would do anything for. But remember that every single day of your life is going to be play, because you’re going to be doing the thing you love.

The next Trailblazer’s Retreat is set for Costa Rica in February 2015. Visit for details.