Timothy Carlisle: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

An Interview With Jake Frankel

13 min read

·Jan 7, 2024

Do the work no matter what — Things are not always easy, nor are they fun. However, when you continue to make it happen, it often provides you with the opportunity you seek. Remember, if things were easy, everyone would be doing it!

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked on Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Timothy Carlisle, CISSP, PMP, DTM, PDD, who has a very diverse leadership background.

Tim spent 20 years in the Submarine Service. He served on four different submarines, rising to the level of Chief Petty Officer. He co-wrote many of the instructions for protecting data and computers in sensitive installations and, at one point, saved the Navy $23 million in today’s dollars by writing a manual describing the detailed operation of a highly classified system.

Timothy has worked as a project director and cybersecurity expert in the public sector and as a consultant. His consulting engagements included eBay, Starbucks, Sutter Health, and other large organizations. He is certified as a CISSP and PMP, both gold-standard certifications in Cybersecurity and Project Management.

He has earned 4 degrees: two Bachelor’s — in Technology, and Operations Management from Excelsior College; Master’s Certificate in IT Project Management from George Washington University, and Masters Degree in Technology Management (Information Security with Distinction) from Capella University.

In his volunteer work, Tim currently serves as the Chief Technology Officer and Western District Five Commander for U.S. Submarine Veterans Inc., Toastmasters Past District 4 Director (San Francisco and Palo Alto, CA), and is an Event Leader in Landmark Worldwide.

He has received a number of awards, including a Jefferson Award for Public Service, the Joe Negri Award (highest award for leadership), and two Robert Link National Commander’s Award from the U.S. Submarine Veterans Inc., the Excelsior College C. Wayne Williams Award for Public Service and Community Involvement, a California Legislature Proclamation for feeding homeless and needy children, and California’s first National PTA award for the academic program he led at Mare Island Elementary School. He has also earned two Distinguished Toastmasters designations.

The opinions given here are his own.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Mychildhood was a mixed bag. My parents adopted me and my brother and sister (all from different families) and cobbled us into a family. As a child, I dealt with childhood trauma and extreme bullying. I watched other people who dealt with this issue spiral down to addiction and suicide. Having an outlet (a parent’s friend from church), I was able to avoid this. I determined that joining the Navy and leaving where I grew up was the best choice for me.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“I would rather be ashes than dust! I would rather that my spark should burn out in a brilliant blaze than it should be stifled by dry rot. I would rather be a superb meteor, every atom of me in magnificent glow, than a sleepy and permanent planet. The function of man is to live, not to exist. I shall not waste my days trying to prolong them. I shall use my time.” Jack London

Most people in my age group are contemplating their retirement, where I am determining what my third chapter will be. I know that entrepreneurship and making the biggest difference for others are my top priorities.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Resilience — Dr. G, a noted psychologist, told me I was the most resilient person he had ever met. Surviving my childhood trauma and extreme bullying, (which made me the ultimate people pleaser), and reinventing myself, were only some of the things I dealt with. I now own my power, which I believe is responsible for lifting me up.
Insane Work Ethic — My mother pushed me to develop this amazing work ethic that goes way beyond the norm. Getting things done no matter what happens has been a large part of my success.
Honesty and Integrity — Telling the truth no matter what — even when you do not look great. Many times, your team can easily recover when you tell the truth. Likewise, doing what you say you will do, no matter what, is a hallmark of integrity, and becoming a go-to person.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

After two years of training, I served on three consecutive nuclear fast attack submarines for the next eleven years. Qualifying in submarines is like taking a four-year college degree, shortening it to 12–18 months, learning all kinds of things outside of your chosen career specialty, and being examined for three hours by four individuals who know about 10 times more than you to see if you meet the minimum required to earn your submarine dolphins. Oh, and after you receive your dolphins, then the real learning begins.

This is the environment where I truly became an adult, responsible for myself and others. Many fine Chief Petty Officers aided in my development — a CPO is like a middle-level manager in the corporate world, adding life coaching skills in many unique ways.

And how did you “reinvent yourself” in your Second Chapter?

After completing twenty years of service in the Navy as a very skilled technical leader, I left the military and moved back to the Bay Area. Due to the lack of distance learning at the time, I went on a tear in the education direction, finishing my four degrees. I also completed several high-end IT certifications.

I did all this while working full-time, serving as an IT Project Manager for a group of elected officials, which may have been a greater education than all the college courses I was completing. I learned how they managed their constituents’ concerns, which was truly eye-opening, and their deft methods of dealing with people and personalities will stay with me for the rest of my days.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

Having completed the educational goals and work responsibilities, looking back, I believe that the trigger which started me on this journey was the union at my workplace requested that I become our representative to the local labor council, where I attended meetings and interviewed political candidates. By doing an excellent job in this area, it gave me the courage and confidence to take the plunge and led to other future leadership opportunities.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Executive Leadership. As a Chief Petty Officer, I was middle management. While I may have aspired to executive leadership, looking back, I did not have the skill set nor the patience.

Thanks to a weekend seminar, I was able to put down the things that were in the way of my success, and I realized who I could become in the future. I continued discovering what stopped me and applied myself, stepping out of my comfort zone for several years to change my perspective and attitude.

That discovery provided the transformation needed to be my best self and become who I am today. Like my friend, Kevin said, “It’s not just that Tim is here — it’s what he had to overcome to get here.” This was said while I was being roasted — but what he said was 100% true.

How are things going with this new initiative? We would love to hear some specific examples or stories.

In 2016, I was elected and honored to lead the Mare Island Base (Chapter) of USSVI. This was an interesting experience where I dealt with a multi-generational team whose shared experiences bind us together like no other. I led our chapter for six years, dealing with a myriad of issues, including bank fraud (not one of our members), relief of a key leadership team member, moving our organization to Zoom during the pandemic, and rebuilding our relationship with the board of the San Francisco National Park Association, which cares for the USS Pampanito, a WWII Museum submarine.

In 2021–2022, I was elected and privileged to lead our Toastmasters District with 3500 members and 120 chapters after four years as a District leader. This covered San Francisco, the peninsula, and south to Palo Alto. This required major stretching on my part — leading folks the average age of 30, incredibly diverse, while during the pandemic, and everything was online.

In 2022, I took on an exceedingly difficult project for the United States Submarine Veterans Inc. (USSVI) regarding their website and database. Based on our success in this endeavor, I was appointed as the Chief Technology Officer. In 2023, I was honored to receive the Dominic “Joe” Negri Award, which is USSVI’s top award for leadership.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am turning this question on its head and telling you about my team doing the impossible.

Bill — an expert database administrator and developer who runs large medical databases, took seven databases with multiple primary keys and figured out how to combine them and only have one primary key. All done in six weeks’ time (not sure that he slept at all!) This allowed the project to be successful. This was believed by many leaders to be impossible.

Gerry — An ace coder and website developer, he backed up and moved a 1400-page website and seven databases to a new location and changed out the old-school 726 database connections to something that was safe to use. When we checked his work via security scorecard software, it was the highest score we had ever seen. This also was believed to be impossible.

Vinny — an expert researcher who moved mountains when it came to finding data and reviewing pages etc. Vinny also provided training to all our 400 members who need to access our backend software.

Dennis — the number one super user in the organization and National Office Manager — his input and expertise were critical to ensure our system functioned. He also provided Chief Warrant Officer to Chief Petty Officer Counseling for me (more of a one-way communication) whether I needed it or not (I usually did)!

My Schedule for 7 months

Can you share the most interesting story that happened to you since you started in this new direction?

When I was the Program Quality Director in Toastmasters (#2 position), President of my USSVI local chapter, and during an intense leadership program, the above pie chart shows my time investing in myself. Amongst everything I engaged in, I think it is safe to say that was almost more than I could handle.

This effort allowed me to tremendously develop myself as an executive leader, building new teams and encouraging teamwork in all the organizations I support. This was the transformation I was looking for, and it changed everything for me.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I believe that everyone who attempts something of significance struggles with this, especially if it is something new. As a leader, having the vision to see what is possible, the solution, the confidence to find the team to make it happen, and the perseverance to see it through makes the person a little crazy at best.

I certainly was no exception. When we got stuck during the project on the database connection issues, I wondered how we were going to resolve this. Fortunately, Gerry had a colleague who figured it out gratis for us, for which we are forever grateful. We accomplished something far greater than ourselves, which seemed daunting, and became doable over time.

For me personally, a leadership class I successfully completed has been described by others as going through the eye of the needle. It made such an impact on me, there was an enormous shift in my perspective, that I now know I can accomplish anything I set my mind to, with enough time and effort.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I will discuss two members of my support team, Pete and Barry.

Pete — When I became the Base Commander (president of my local USSVI chapter), in the first two years, I dealt with many sensitive and critical issues, all of which I previously mentioned above.

Pete and his wife, Debbie, were my biggest cheerleaders in this leadership journey, and he appointed me to his former role when he moved up! He also helped me understand and develop the skills and savvy necessary to become successful in that role.

Barry — a colleague with great skills in the world of politics and USSVI, provided me with timely advice while facing one of the biggest challenges in my leadership journey. When wrongfully accused of a violation in a different organization, he helped me skillfully turn the tide and made the difference between success and failure.

There is no question in my mind these folks made a huge positive impact on my life as my support system, for which I am forever grateful.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I had struggled with public speaking since a small child, so I joined Toastmasters. My first speech was supposed to be between 4–6 minutes, and it lasted 15 minutes (I was jokingly told I might want to shorten it just a bit)! Despite that inauspicious beginning, seven years later, I was privileged to lead 3500 Toastmasters and 120 chapters from San Francisco to Palo Alto during the pandemic.

What are your “5 things I wish someone told me before I started” and why?

1. Have a plan — Begin with the end in mind (Stephen Covey). If you want to lead an organization, have a development plan to do that. I also recommend finding a mentor to help you navigate the people and personalities who are part of that organization.

This has proven extremely valuable to me in everything I do, at both work and volunteer efforts. The plan will change and adjust; it may even grow! If you keep putting the work in, you will get there!

2. Be curiously engaged — While someone said curiosity killed the cat, it also made the leader! Be curious about why others feel the way they do — big bonus points if they feel differently than you do. This provides you growth and understanding, which has several times saved important initiatives I have pushed.

3. Be open to new opportunities — When we start on something new, we do not necessarily envision where it will take us. Be open to saying yes to growth opportunities when they arise. They may take you to the very top!

4. Believe in what is possible — So many times, I believed before things happened. Create what you want to achieve, then live into that future — it will rock your world as it has mine!

In USSVI, I created the possibility of completing a huge project in five months, whereas other companies could not complete it in eight years.

5. Do the work no matter what — Things are not always easy, nor are they fun. However, when you continue to make it happen, it often provides you with the opportunity you seek. Remember, if things were easy, everyone would be doing it!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I am committed to creating a world that works for everyone and empowers people to be their best selves, no matter their circumstances. I also am for improving communication and leadership in the world.

Perhaps a leadership program for people who have dealt with trauma, I have seen many people who have past traumas are not the leaders they could be and some of the smartest and most creative people I know shy away from leadership because of their lack of confidence that comes from past traumas.

Having a program to help those people get past their trauma and discover their power and leadership, I believe, would benefit not only the person but all the people they would impact for the rest of their lives. They would also become the leaders of the nation, which would have a massive impact on how our country operates and the future of our world.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Tim Grover — Tim was Michael Jordan and Kobe Bryant’s trainer and has authored several books, which I learned from greatly.

How can our readers further follow your work online?

https://www.linkedin.com/in/timothycarlisle/
https://timothywcarlisle.com

Thank you so much for sharing these important insights. We wish you continued success and good health!

Thank you — I really enjoyed the experience!

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