Young adulthood is one of life’s great opportunities to slow down and figure out who you are.
Success is something each person must define for themselves. Yet without pausing to slow down and reflect, many of use move through our formative years without ever truly checking in with themselves. Stephen Covey calls it stopping to sharpen the saw. My coaching creates an opportunity to get clarity, build self-confidence and establish a positive and resilient attitude towards your life’s journey.
A Message for Young Men
You’re not supposed to have it all figured out yet. If you’re in your late teens or even late twenties and something feels off — you’re not alone. A lot of guys today are stuck in a strange place: the future feels uncertain, and the path forward less clear than ever. You might feel behind, unmotivated, or unsure what you’re even working toward. And it may feel like the people around you don’t get it.
What you’re really looking for is clarity, self-confidence, and some optimism. Clarity isn’t something you chase. It starts with slowing down and talking honestly — about what excites you, what drains you, what feels right and what doesn’t. The answers are inside you, you just need to take the time to listen to yourself. Coaching conversations is where clarity begins to show up.
Self-confidence grows from recognizing there is no one else like you and life isn’t a competition. Your path is your own to forge. Coaching can help identifying your strengths, challenging beliefs that may be holding you back, and stacking small wins add up and motivate you to keep having fun moving forward.
Optimism is about living in the present with an gentle eye on the future, and letting life unfold for you. Developing a positive attitude is a superpower.
Having a coach is a real opportunity — and, in many ways, a privilege. The best athletes and executives in the world have coaches. It’s how high performers operate. You may have had tutors and college prep counselors, coaching is a continuation except you are in charge. If you are looking to get clear on who you are and where you are going please reach out for a free 30-minute call.
A Message For Parents
What young men need most today is clarity, self-confidence, and optimism. Clarity about who they are and where they’re headed. Self-confidence rooted in their own uniqueness and a genuine belief in their abilities. And optimism — a real sense that life will unfold for them and work out. These traits are not as easy to come by these days as we all feel the effects of smartphones, social media, and constant digital stimulation on attention spans. In addition the constant comparison that started as a child and continues to this day, prevents young adults from seeing the world of possibilities available to them. AI is now reshaping careers in ways that feel impossible to predict. For many young men, these pressures show up for them in feeling stuck, distracted, and anxious and even depressed. Many young men hide their true feelings from friends and family.
As parents, you’ve likely done far more right than wrong. You’ve invested in his future in many ways — tutoring, test prep, college advisors. All worthwhile. But self-discovery is arguably the most important work of this stage of life, and it’s also the most overlooked. As a parent there is only so much your own child can take from you as they are in the stages of individuating making even the best parental guidance hard to hear.
What I offer your son is something you can’t give him yourself — not because you aren’t capable, but because you’re his parent. I’m a neutral, confidential presence in his life: someone he can be completely honest with, who will ask him the hard questions, and who will help him figure out what he actually wants — not what he thinks he’s supposed to want. When a young man gets clear on that, everything shifts. He becomes more focused, more motivated, and more grounded in who he is.
If that sounds like something your son could use, I’d welcome a conversation.
What I Do
I work with young men starting at college age and beyond. Whether you are just starting your independent journey outside the home or starting your career as an employee or as an entrepreneur – I help you navigate these pivotal years.
As a certified life coach, I don’t tell my you what to do or who to be. I just help you see blind spots and help you get in touch with your authenticity and listen to true yourself. Each of us has unique gifts, strengths and intuition. I help you embrace your strengths and desires and make your life happen for you.
Coaching is not therapy. I am not diagnosing or treating mental health conditions. Coaching is about self-discovery and moving forward. I provide a safe, confidential space to slow down, reflect, decide and take action. I also help you stay accountable to your stated goals. Only through experience can you build self-trust and confidence.
My clients and I discuss anything and everything from where and I not living my truth, to how to deal with school, work and romantic relationships. There is so much to learn when a situation arises that needs attention or is triggering. We break those down, you can see the situation in a way that serves you and matures you.
I draw on a range of tools and concepts, including meditation and philosophy, and I use an assessment called the ELI — Energy Leadership Index, which helps clients understand their default attitudes and how those attitudes shape their lives. I frequently suggest books that can open up new ways of thinking and spark meaningful conversations. I believe reading important books is one of the best ways to find out who you are.
Socrates said, “The unexamined life is not worth living.” These early adult years offer a rare opportunity for a young man to pause and reflect on who he is, what he truly wants, and how to approach life’s lessons with a spirit of curiosity. I strongly believe that life has a way of presenting us with exactly the lessons we need, in the form of the things that challenge us most.
How Coaching Works
We meet virtually 3- 4 times a month. We evaluate your satisfaction at 10 different parts of your life. And we set out to work on your top priorities. Along the way, things come up. Each week, in each session, we set out what it is we want to work on so that you know you’re making progress. We can also set longer-term goals, track them and overcome what might be standing in your way.
You’ll:
- Get to the root issues and beliefs that are holding you back and replace them the new ways to show up.
- Clarity on your “why” and your definition of success
- Deeper self-awareness and uncovering limiting beliefs
- Greater motivation through personal accountability
- Confidence in speaking up to advocate and set boundaries
- Greater self-confidence, less anxiety, and more joy
- Healthy attitude on your life journey
About Me
My first job after college was with Goldman Sachs — not the right fit for many reasons. I left for an MBA at Columbia, then joined J.Crew corporate, then left to start businesses of my own. I became a commercial real estate broker along the way. All in, I must have tried five or six things before a partnership with my brother-in-law didn’t work out after just one year. At 29, newly engaged, with no visibility on my career I felt I had hit rock bottom — scared, depressed, and frustrated.
Like many of us, my own childhood had its challenges. I navigated family difficulties, changing schools, and a persistent struggle to feel confident and accepted among my peers. I went to college to study architecture, then switched to finance after one semester.
That was probably one of the most important and meaningful times in my life. I needed to dig deep and work my way through it myself. I wouldn’t change a thing about that journey. It was where I first learned to appreciate my own unique path — and discovered an enduring lesson: that eventually things work out, and every scary challenge in life is really the universe delivering exactly what you need to grow.
When I reflect, I think I was living so much for the expectations of others — trying to impress, trying to fit in — that I never stopped to check in with myself. I frequently felt alone, disconnected, and dissatisfied, sensing deeply that I wasn’t living in alignment with who I truly was. And yet I kept searching for that next job, that next thing, that would finally make everything okay.
It wasn’t until I worked with a coach that things began to shift. I was asked to slow down, look inward, and check in on my values, how I was showing up and what was truly important. That experience was transformative — and it inspired me to do this work for others. I believe deeply that when young men take the time to truly know themselves — not who the world tells them to be, but who they actually are — everything changes.
I bring to this work something most coaches can’t offer: a well-rounded combination of personal experience, a parent’s perspective, and hard-won business and leadership expertise — alongside a calm, grounded presence shaped by years of yoga and meditation practice.
▶ Business & Leadership
After roles at Goldman Sachs and J.Crew Group, I founded ePromos Promotional Products and grew it over 21 years to high eight-figure annual sales with 175 employees before selling it. I hold a B.S. in Finance from Syracuse University and an MBA from Columbia Business School.
▶ Certifications & Practice
In 2021 I earned my life coaching certification through iPEC — one of the most respected professional coaching organizations in the field. Since then I have worked with businesses and business leaders, and have recently made the deliberate shift to focus exclusively on young men — the work I find most meaningful and impactful. I am also a 200-hour RYT certified yoga instructor.
▶ Life & Wellness
I am a father of two young women in their twenties. My wife and I recently co-founded HapBE Valley Equine & Wellness Farm in Asheville, NC, where I facilitate Equine Facilitated Experiential Learning and lead meditation and yoga practices. For six years I have led a meditation group that meets five days a week. Outside of work I enjoy strength training, pickleball, golf, building and fixing things on the farm, and keeping up with AI and the business world.
▶ Young Presidents’ Organization (YPO)
I’ve been an active member of YPO for nearly two decades—a global network of chief executives committed to becoming better leaders. The organization has played a meaningful role in my growth, both professionally and personally. Through YPO, I had the opportunity to study in the Harvard Business School Presidents’ Program in Leadership, an intensive executive education experience available exclusively to members. Some of my clients are children of YPO members.
Testimonials
“I recommend Jason Robbins to coach your young adult. While I enjoy a close relationship with my college student, there are just some things he can best open up about with a confidential and trusted third party. Jason’s background as a business leader and executive coach gives him the credibility to earn the respect of our young adults. He asks the right questions, peeling back what’s really important and what my son is truly striving for. My kid has a stronger sense of himself now. Jason helps keep him grounded and far less influenced by the significant social pressures surrounding him.”
— G.B.S., Palm Beach, FL
“Having a Jason as a coach, has opened my eyes to underlying problems I hadn’t been facing. He helped me opens up solutions and see different perspectives and makes me think harder about my own values and desires. He is helping me find my path and appreciate the journey. I think everyone should have a coach like Jason!”
— S.L., University of Chicago
“I’m a young CEO and tasked with turning around a distressed eight figure consumer products business, and started working with Jason as a coach. Through Jason’s guidance I am able to up level my management skill set. I learned how to interview properly, hold people accountable, get the right people in the right seats, use 90-day planning cycles with trackable goals, build a scorecard, stop micromanaging and utilize my leadership team. In less than a year we’ve turned the company profitable. I would highly recommend Jason to entrepreneurs and executives of all experience levels that take their personal development as a leader seriously.
— B.B., Boca Raton, FL
Let’s Talk
If the idea of examining life and build a foundation for happiness rooted in his own wisdom resonates with you — this conversation is worth having.
Complimentary 30-Minute Discovery Call
No pressure. Just a conversation.
“To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment.”
— Ralph Waldo Emerson