An entrepreneur, strategist, and consultant, Chase Damiano helps others achieve their wildest dreams. By applying proven methods to help his clients identify where they are heading, who they want to be, and how they’ll get there, he can always be seen as a partner to your success. “


  1. At the end of the day, only you are in charge of your life. When it comes time to make even the toughest of decisions, you already know what I need to do; deep down inside, the answer lies within.
  2. The important thing to identify is something that gives you strength. Jumping out of bed with a passionate feeling, and being rooted in the reasons why you’re there can really be a sustainable wealth of energy
  3. Know that everything you are doing today, in this moment, is temporary. There is a grander context for our lives than just this job or “x.” Every experience has an opportunity to be a set of training wheels as we prepare for the way that we’re really going to impact the world, in the most meaningful way possible…

Transcript: The One Away Show Featuring Chase Damiano

BRYAN WISH: Welcome to the show, Chase. What was your One Away moment?

CHASE DAMIANO: My original endeavor into entrepreneurship was a 5-year career with a startup here in the D.C. area called Commonwealth Joe. At this point, it’s now grown into a regional coffee brand. I loved that startup. It gave me a tremendous amount of energy, joy, and passion.  These are just a few of the things that really hook many entrepreneurs in; being part of an experience like mine.

Back in June 2019, I made the hardest decision I’ve ever made in my life. The difficulty of this decision went beyond any I’d ever made before. I made the choice to leave that startup, after five incredible years. What I did next was really unique. I took a 12-week sabbatical that totally transformed my relationship with work, with others, and most importantly, with myself. 

BRYAN WISH: Can you tell us a little bit about what led up to that decision? Describe how you were feeling about everything before leading up to that decision. 

CHASE DAMIANO: For entrepreneurs who are starting companies, there’s usually a strong emotional attachment they may have with the company where they start. Maybe this is born out of a particular passion they have, one that they want to translate into a business. That was certainly the case for me.

I’ve always loved coffee. I love creating companies. Joining these two passions together made this endeavor a really important milestone in my career. At the time, I felt like we reached a point in the company’s development where it would better serve the business to have someone new take the reins and pick up where I’d left off. 

At that point, I’d finished building the internal infrastructure in the company. We had processes to clarify everything from big picture goals and vision down to the day-to-day activities that served our customers. 

The startup had strong individual and team member alignment. I felt that a change of guard could better serve the needs of the company as a whole. Bringing in someone new could even create an opportunity to provide an internal promotion to a worthy teammate. 

To be honest with you, I was also quite burned out. I had put a tremendous amount of my lifeforce, if you will, into the company to get it to that point. I certainly needed a break.

BRYAN WISH: It sounds like that led you to a pretty transformative experience. Tell us about the sabbatical and what you learned about yourself when you took some time to fully focus on you.

CHASE DAMIANO: Arriving at the decision took quite some time, thought, and effort. I had spoken with a very large number of leaders and executives who I had either known or recently met via networking to discuss this very challenge.

I asked each of them to sort of put themselves in my shoes and ask, “What would you do in this post-startup experience?” 

Based on the responses I heard, it seemed like a lot of roads led to taking a sabbatical. I sent a very long, verbose email to my closest peers. I wanted to share exactly what I would be doing with this time while I was disconnected. I completely turned off all my emails and text messages and canceled all my phone calls and meetings for eight weeks straight.

After that period of being totally off the grid, I transitioned into a slow, four-week reconnection period. It wasn’t completely absolute. I still had a whitelist of very close family members and friends who I was still in contact with from time to time. The main idea of it was to disconnect, go off the grid, and just spend some time with myself. 

During that period, it was really eye-opening. During the first several weeks of my sabbatical, I still felt the urge to be productive. I had this nagging need for an output for my time; something to show what I’d accomplished during my time away. 

It took about three of the eight weeks to spin down and shift my mindset. I started off feeling like I needed to provide proof or show what I’d gotten from this experience. It took a while to really tune into more into my internal desires, inner voice, and intuition. 

The capstone of my sabbatical was a two-week silent meditation retreat down in an Ashram called Yoga Village, just south of Charlottesville, Virginia. All I did during that period of time was the following: 

  • Exercise
  • Meditate
  • Eat
  • Read
  • Write 

Being in this environment created the amount of stillness that I was really searching for to finally wind down from my high energy, intensive, passionate work in a startup. At the retreat, I could begin to slowly rediscover the entrepreneurial energy I had within me. 

BRYAN WISH: When you were silent for those two straight weeks, what was going through your mind? What did you reflect on in your past that maybe helped catapult some of your ideas forward to what you’re doing now?

CHASE DAMIANO: During the silent retreat, I had a remarkable experience within the first day or so. It’s the sort of the effect you have from the phantom vibration on a cell phone if you constantly have the vibration on. You develop this urge or compulsion to talk to, relate to, or communicate with others in your immediate vicinity. 

This urge is a very human thing to want to do. It’s a natural part of who we are. As that need dissipated, I focused a lot of my writing, meditation, and reflection on a very close examination of the mental chatter going on inside my own head. 

Each of us have our own inner voices. We also have different voices and archetypes in our minds. Sometimes the voices of our parents speak to us through our minds; our children might do so, too. These inner voices could come from anyone important in your life: 

  • Friends
  • Family
  • Peers
  • Former significant others or romantic relationships

Our inner dialogue is composed of voices from all the different parts of our past. It’s really just an appearance or embodiment of some emotion you’re having. I wanted to take a very close examination internally. I really tried to understand the stories that I was telling myself as they related to three critical dimensions of my life: 

  • Work
  • My relationships
  • My own identity

This insight was the most significant one that came from the meditation retreat. When you slow down enough, all you have to deal with is the mental chatter happening within your own mind. This gives you an opportunity to see these thoughts for what they really are. At the end of the day, all it is is chatter. 

BRYAN WISH: You said that something that you learned from this is that when we’re career-oriented, sometimes we leave our families or personal relationships and even lose sight of ourselves. I think you’re right. To an absolute degree, we definitely can. 

I’d like to ask a counter question about this experience. As you made this hard decision, do you think it was maybe necessary to leave some of these relationships behind that were from the past, in search of finding the better path that was really meant for you?

CHASE DAMIANO: I think with every major change that happens in life, there are going to be reasons to do it and there are going to be reasons not to do it. There are advantages, disadvantages, pros and cons to using an oversimplified decision-making model. 

Surely in leaving my previous company, I had to leave a tremendous number of relationships behind. Fortunately, after coming back on the grid, the context for those relationships completely changed. 

No longer was I inside a company with these other folks as peers, direct reports, team members. Now, I had the opportunity to form these into new relationships with new contexts, ones I could create outside of work. This was an unexpected benefit. I realized I’d be able to still maintain great relationships with the folks who were still within the company. I had anticipated something like this happening to a degree, but I was pleasantly surprised by how great it turned out to be.

BRYAN WISH: You wrote something to me about how in the process of making this decision, you can get all this input from others, but at the end of the day, it’s your decision to decide your own fate for your own future. 

I was listening to a podcast this morning with Naval Ravikant and he said, “The best founders I know are the ones that take information from the collective whole and then make the decision that’s best for them, even if it doesn’t agree with the people who gave them advice.” You collected all this information, and I’m sure you had a lot of conversations before this decision. What did this experience lead you into? 

CHASE DAMIANO: Sometimes when we face a difficult challenge or are looking for answers, we might do a number of endeavors for outreach and information collection. 

Usually, we solicit and gather input and feedback from our network:

  • Friends
  • Family
  • Peers
  • Coworkers. 
  • Advisors
  • Coaches
  • Mentors

Ultimately, we lean on people who might have been there before and are more experienced. 

Sometimes, this process might look more like research:

  • Reading books
  • Listening to podcasts
  • Reading articles about the topic

Some people simply Google “What should I do?” 

I think you can get a tremendous amount of input to support your decision-making process. Everyone is going to have different perspectives based on the context of their own experiences. 

Yet, there’s a difference between collecting this information and actually making the decision. You might receive all of this input, and it might influence your opinion, but in the end, you get to make the final call. You get to make the actual decision. 

Going through this experience taught me that at the end of the day, we truly are in charge and responsible for our own lives. We decide how we want to live them. We get to make the final decision on every decision that we make. 

Coming to this realization taught me that when I have to make my toughest decisions, I already know what I need to do. Really deep down inside, the answer lies within. I believe this is often the same for most of us. There’s a part of us that already knows three core truths:

1. Who we are

2. Who we can become

3. What we need to do in order to get there

Having been through this experience of really reflecting on my own purpose, now I know my reason for getting up in the morning is my community. In my case, this is other entrepreneurs. I feel very strongly aligned with the business community, founders, executives, other leaders. 

For many reasons, I understand how tough it is to be an entrepreneur. The journey can be so lonely sometimes. It can be so isolating between employees, investors, other coworkers, peers, and even friends and family members. 

I seek to create a world in helping founders and executives and other leaders be able to manifest their vision. Nowadays, I run an early- to mid-stage consul tancy and advisory practice to help entrepreneurs get out of the weeds and start thinking more strategically.

BRYAN WISH: Your process that you’ve used in this decision making, from leaving the startup to now coming into your own, is how you help other entrepreneurs make clear decisions. That experience has really helped you help other entrepreneurs navigate this lonely journey. Can you maybe speak to that and how you’re going about doing that to help other people do the same?

CHASE DAMIANO: Sometimes when we are building our companies, certainly we have a reason for doing so. We always have some sort of purpose or original intent; whether it is a customer segment that we seek to empower, all the way to thinking “I just want to make money.” Each one is a reason in itself. 

Sometimes along the journey, as we are building our companies, we get all this input from other investors, from customers, from employees on where to take things. I think being deeply rooted in one’s purpose, specifically as a founder, specifically for the reasons that they got into this in the first place. 

This is an important part of staying in tune on that journey. There might be a new opportunity to start climbing a mountain, only for you to realize that the mountain that you’re climbing is not the right one. 

Many times, I’ll speak with founders or their individual team members and we’ll talk about why they originally joined this company. For the founder, this would be why they started their company. For a team member, this is why they ended up joining. You’ll hear different answers. 

Ultimately, you’re trying to answer this question across the board:

“What does employment or association with this company mean for each of them in the end?”

Sharing these responses across team members within a company can really be transformative. It can even help identify the major themes in common across the team, and why everyone is there. 

Having clarity on such a purpose, such an intent, can create a lot of energy and strength. This is especially useful when going through the tolling details of building a company. Not every aspect of any role or position, even as founder or on the executive team, is going to be sexy. 

The important thing to identify is something that gives you strength. It’s something that gives you energy and motivation. Jumping out of bed with a passionate feeling. Being rooted in the reasons why you’re there can really be a sustainable wealth of energy as you go through those tiresome details. 

BRYAN WISH: You’ve experienced a lot of change in the last eight months leading up to this decision, making the decision, and everything that’s followed since. What has it felt like to stand out on your own and fully embrace this new journey as one that you have full ownership over?

CHASE DAMIANO: This whole experience, from taking a sabbatical to now help other entrepreneurs with similar decisions and building their vision, has made me feel like myself. I think that might be the best way to put it. 

I believe that each of us comes to the table with a unique set of strengths. We’re not strong at everything, and that’s okay. We’re not meant to be. Based on our unique set of strengths, we can find opportunities to apply them in various ways that are uniquely beneficial to whomever the recipient might be. 

What can we be doing to help others? How can we help make change into the world? After going through this change, I feel:

  • More self-connected
  • More self-aware
  • Healthier
  • Tremendously happier
  • Much more inspired
  • Creative
  • Exploratory
  • Intuitive in many new ways. 

Those are the qualities that I always saw myself. Now, I finally have the ability to express these strengths deeply and very fully. Now having gone through this change, I just really feel like myself. I feel I’ve finally become the person I’ve always seen myself as being. That is very powerful. 

Life can be serious, but we needn’t take everything so seriously. There are elements of joy and fun we can weave into every day, even in the face of high amounts of stress. Now, I just feel like I’m having fun in my life.

BRYAN WISH: As you’ve fully come into your own and you feel like yourself, how has that come through tangibly both in a personal and professional setting?

CHASE DAMIANO: As I work with other founders and executives, I’ve seen a commonality. They all have a hyper-attention on their companies doing right by their employees, investors, and customers. There tends to be a sort of pulling in multiple directions, or a wearing thinnedness, if you will, or feeling lost and uncertain. 

So many of them express a feeling that everything is breaking, or there are too many fires to put out. The way that I like to help others is first, with much reassurance. I reassure them that all the issues that are happening as we grow our businesses have happened before. We’re not the first ones to encounter all these issues. Others have solved them before.

After giving them that reassurance, we move onto context and perspective. Then, we actually start to shift from the problem into what the solution can be. We assess if the solution we brainstorm is warranted. 

Sometimes just speaking about the problem is more than enough. For me, this manifests in an ability to relate and see more clearly that these are solvable challenges. In the end, this manifests in a feeling of not being so alone on the journey anymore. 

BRYAN WISH: If someone was in your shoes around the time you were making this decision,  and they were really struggling between the hard answer that they know is the right one and the one that is safe and comfortable, what would you leave them with? 

What would you say to them so they feel more able to go out and be the courageous one to stand out like you’ve done, and to feel like their full selves?

CHASE DAMIANO: If someone is in my previous shoes, my advice is to know that everything you are doing today, in this moment, is temporary. There is a grander context for our lives than just this company. Every experience has an opportunity to be a set of training wheels as we prepare for the way that we’re really going to impact the world, in the most meaningful way possible.

I’d suggest that anyone in that position should take time to reflect on the original reasons that they joined the company. Perhaps I’d ask them to review past journal entries and get some feedback from close peers, friends, or family members. It’s likely what you’ve been telling people lately includes indications or symptoms of misalignment.  

Hearing your thoughts in a fresh light from friends and family, the closest people in your network, will help you to see the state you’re in today. Developing a clearer view of what’s happening right now might necessitate making a change.

BRYAN WISH: Where can people find you?

CHASE DAMIANO: You can find me at, and I’m on LinkedIn as well. I’d love to connect and talk. If I can be helpful to even one single person who is listening to this, it’s all worth it for me.