E37: What’s Next | Maximizing Your Life - Ann Bernard



Laurie Barkman is joined by Ann Bernard, author and creator of the 365 Firsts challenge. Ann shares her journey and how she navigated several transitions in her personal and professional life. Her story will inspire and challenge you to re-evaluate your journey and find the strength within to press on even in the face of seemingly insurmountable odds.


Listen in to learn more about:

  • How self awareness can help you align with your purpose

  • Learning and growing from failure

  • Adapting to change and disruption


Show Links

Ann Bernard’s YouTube Channel

365 Firsts YouTube Channel

First Time Storytelling YouTube Channel


Connect with the host, Laurie Barkman on SmallDotBig.com and sign-up for an insights newsletter to build value in your company.




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Episode Transcript


Welcome to the Succession Stories Podcast, I’m Laurie Barkman. I work with business owners to maximize value, create options for the future, and be happy in your next.

I’m excited to share the “What’s Next Series” as part of Succession Stories.

These conversations spotlight the theme of transitions.

Changes can come at you unexpectedly, or be planned. Are you ready?

After all - in business and life – succession is about transitions and how you embrace “what’s next” matters.

Laurie Barkman:

This week I was joined by Ann Bernard, CEO of 365Firsts, and creator of the 365FirstsChallenge App and the First Time Story Map Project.

We talked about Ann’s journey from decades in the Marine Corp to serial entrepreneur. It hasn’t been an easy road. Ann started and failed multiple businesses, and bounced back from depression and debt.

After her failures, Ann found herself on a journey of first times and new experiences that completely changed her relationship with life. Now her world revolves around leading others to discover new experiences, understand who they are, and maximize what we get out of life.

For anyone thinking about transitions, I hope this episode helps you think differently about finding what’s next in your future.


Laurie Barkman:

When you face your biggest ownership and leadership transition decisions, will you be ready?

Most owners feel as if they are pushed out of their business but the happiest exits occur when there are more factors pulling you towards your next.

That’s why I’m offering a way for you to evaluate your readiness on a personal level

Go to: Getmyprescore.com


Take our online survey. It takes just 8 minutes to complete, and you’ll receive a custom report of your Personal Readiness to Exit your business, including a summary of unseen factors that could lead to regret.

In addition, you’ll also receive a free eBook, “The Exit Checklist: A 5-Step Personal Action Plan For A Happy (And Lucrative) Exit From Your Business”



Laurie Barkman:

Ann Bernard, welcome to the What’s Next Series. I'm looking forward to our conversation today. You have a very interesting and unique background, and your past has brought you to your present, and what you're working on in your future. I thought it'd be really interesting for you to start out by sharing your story. What's your background? Where did you grow up?



Ann Bernard:

I was born in Edmonton, Canada. When I was just a baby, my parents moved back to the province of Quebec in St. George, Canada. So I grew up there. At the start of my sixth grade, because my dad was working construction in the US, we moved to Palmer, Massachusetts, and I went to grammar school there. Moved there, I didn't know any English, I went to grammar school, high school. At 16 years old, I fell in love with the Marine Corps and at 17, I was in boot camp. I turned 18 in boot camp.



Laurie Barkman:

So the Marine Corps. What interested you, and why did you choose that path?



Ann Bernard:

It's a mixture of things. My family life was not ideal and I wanted to just start living on my own, be in control of my life. But it's also, my high school sweetheart joined the Marine Corps. He was writing me about all the really amazing things that he was doing and places that he was going to, and I wanted that. I wanted the adventure and I started reading -- this is back in 1995, '93 - '94 -- so no internet to look up things on the Marine Corps. So you went to the library and found the Leatherneck magazine. I just fell in love with what the Marine Corps stood for; the mission that they had, and I just knew it was the right thing for me.



Laurie Barkman:

How long were you in the Marine Corps and what types of roles were you in?



Ann Bernard:

I was on active duty. I joined at 17 as I turned 18, and I did four years as an enlisted Marine. I reached the rank of Sergeant and then I put in for the Meritorious Commissioning Program. I got selected as a Sergeant, I drove across the country and off to OCS, became a Second Lieutenant, and I got to the rank of Captain. On my 10 year mark, there were a lot of different things that were happening, and they say the 10 year mark is the point where you make decisions. Do you go the other 10 or do you call it quits?


For me, I had always had an entrepreneurial desire and drive. So I felt like it was time for me to get out. It just wasn't fun. We have another saying,


"If it's not fun anymore it's time to get out."

And it wasn't fun anymore. So I left active duty, and I started my entrepreneurial journey which led to failures, and I found myself back in and out of the Marine Corps. So at this point, I still need to... I'm waiting for Trump to leave office and then I will drop my retirement papers. But I have 25 years in now and I ended up reaching the rank of Lieutenant Colonel and 16 of those years on active duty. I filled all kinds of billets.


So as a young enlisted Marine, I was in logistics and then I became an officer. As a woman, at the time -- I'm so glad things have changed -- but at the time, the only job at MLS (Military Occupational Specialty) where I would lead at Marines was as a Communications Officer. So it was a no brainer, because I wanted to be a Platoon Commander. So that's what I became, picked up my first platoon and Communications Officer and then I filled so many other billets after that.



Laurie Barkman:

What is the Communications Officer responsible for? Who did you work with most closely?



Ann Bernard:

We set up the communication network. I ended up doing a lot of deployed networks. As an officer, I knew some of the technical stuff, but it was the Marines that were the technical ones. So my job is to take care of them, to train them and to enable them to do their jobs. So we would deploy and set up the networks, obviously you are supporting the mission, you're supporting the warfighter. If you can't talk, you can't fight. Communication is such a critical job to have. Such a critical thing to have in everything you try to do. That was another reason why we have a saying that goes like,


"You can talk about us, but you can't talk without us."


Laurie Barkman:

You can talk about us. You can't talk without us. That makes a ton of sense. So you were working with Marines that were deployed in the field?



Ann Bernard:

Yes. So I had some billets that were deployed in the field and I had some where we managed the networks back in what's called garrisons, so the base networks, and also get involved in the security of the networks. Now cybersecurity is something that's constantly talked about and very important, but back then the CommOs, nobody in leadership liked us because we're slowing down the network because we want to secure the network. There's a lot of things. As a CommO, it can be an extremely high stress. We were talking about that before, right? Comm goes down, they're looking at you, like you can magically fix it. Somebody is usually always yelling at you, because something is not working the way it should.



Laurie Barkman:

Yeah, and me in my office in my safe space when my Zoom goes down, and I'm angry in my head, and I just want to burst. I can't even imagine what that's like, being in the field and comms go down. I can't even compare.


So I appreciate that you had mentioned earlier that you were in the Marine Corps, you were looking for some change, and you had some entrepreneurial ideas that didn't really work out. Can you share a little bit about that period of time? What were you trying out? And what failed? What was it?



Ann Bernard:

Oh, absolutely. So when I first left the Marine Corps, I had heard about life coaching. This is in 2005. Life coaching, while it had been around for almost a decade already, it was still very unheard of, but it really appealed to me. So I got trained as a Life Coach, and I became a Life Coach and I quickly realized, this is not for me. I move at a very rapid pace, and I don't let anything hold me back. Dealing with clients who every little thing is an excuse, I couldn't do it. But I was learning about business and I love business. I'm like, let me switch over to becoming a business coach. I switched to business coaching and I really enjoy working with business owners. But I found myself running their businesses for them, like, "Well, I'm not getting paid enough to do that," and then I realized there's so many coaches out there that are struggling with the business aspect, but they're great coaches. So I just decided to start a coaching agency. So now this is in early 2006.


Well, there's ignorance, right? You don't know what you don't know. And now looking back, I'm like, "Well, that was kind of a dumb move." Because as an industry, it was not ready to support an agency. But I pursued it, and I love technology, so I created a portal that was going to connect clients and coaches and I really got into it. I had a partner that was doing the technical part. Different things happened. He decided I owed him $40,000, and he was not going to give me any of the code. I did not establish the proper legal partnership documents that would have access to that. So that took me under.



Laurie Barkman:

You paid him the money?



Ann Bernard:

No, I did not pay him the money. I did not get the code. But I also realized, the industry can't support what I'm trying to do and so I closed that down. A week later, I was in a Chipotle and I had this other idea for a concept called "Why Go Solo." So I'm sitting at Chipotle all by myself and I'm like, 'How cool would it be if somebody else that was sitting by themselves either had a sign -- now it would be an app -- but had a sign and I could just join them because they were open to, "Hey, I'm having lunch alone, you're having lunch alone, let's have lunch together," and just see where things go. Because I really believe that people are what can propel you. I mean, meeting the right person can change everything about what you're trying to accomplish.


So Why Go Solo came about and I enlisted eight developers from around the world. We were building at the same pace that Facebook was and we were a part time team doing this together. We released the platform, we were tied into Twitter, we were tied into Facebook. Now this is mid 2006 and it was time to raise money. I lived in the Virginia area, I should have moved to Silicon Valley. So I started pitching investors. They didn't get the concept. I mean, I'm talking about social media in 2006. Most of the people I'm talking to don't even have websites. So timing is key as well.


Laurie Barkman:

Yes.



Ann Bernard:

I invested so much in the first business and the second business, and I kept going but eventually I was broke; had to foreclose on my townhouse. That's when a friend of mine was like, "Hey, you're still in the Inactive Ready Reserve for the Marines." And I'm like, "No, no. I'm not; I resigned." He's like, "You are." And so we argued, and he ended up being correct. I had resigned my Active Commission, but I still had my Reserve Commission. So I was in fact still part of the Marine Corps. So that's when I was able to take some orders, get myself financially -- because now I'm in debt. I'm so broke plus I'm in debt -- get myself back on track. I continued to invest money in Why Go Solo, but eventually I had to realize I'm exhausted. A lot of the members of the team had left. They'd given up, it's not happening. I still completely believe in what it was all about.



Laurie Barkman:

If I hit the Wayback Machine website, will I find WhyGoSolo.com?



Ann Bernard:

You should, although there's a new Why Go Solo now and they're doing an app. I know, the concept was always valid. Clearly somebody is now today doing that. Because we were tapped into social media, the other websites, and at one point, I'm like, "Okay," because the way Why Go Solo worked, you would create a listing. So if you had an extra ticket to a concert, or to a game or to whatever, to start going to the venue and say, "Hey, give me some extra tickets, and I'll promote them on our platform, which will promote them on Twitter and Facebook. Because Google ads are going to go away, you're gonna want to be in people's news streams," and again, this is 2006. I'm telling businesses this, but they don't even have websites. So what I'm saying, like they don't understand Facebook, they don't understand Twitter. Really, it took those platforms, Facebook and Twitter, almost a good five to seven years to really raise to the level that they have, the impact that they have now. So that taught me a lot about just how much time it takes for something to take off.



Laurie Barkman:

It really does. And so for you in that phase of your life, you said you lost your townhouse. Were you homeless at one point?



Ann Bernard:

So I was at that point. A friend of mine let me borrow some money and I was able to rent a room. So I move there and then I get back in uniform and back on a salary and I get myself back together. Then an opportunity came up. I was in the Virginia area and an opportunity came up to go to New Orleans and I jumped on that. So I was like, 'I need to get away from the Virginia, DC, Maryland area. Let me go to the Big Easy and see what happens there.' So I moved to New Orleans in January 2009, and New Orleans will always have such a special place in my heart, because there's a lot of healing. It's where I eventually came to my breaking point, but there was so much healing that took place there as well that set my course off in a different direction.



Laurie Barkman:

Well, that's probably a good place for us to change gears a little bit on the conversation, and talk about re-discovery. Because I think, especially for this series, talking to people about changes in their life, changes in their career. Are they going to make things happen? Are they going to watch what happens? Are they going to wonder what happens? And so you're at this pivot point in crossroads, where you're trying to figure out what was next for you. You had some failures, as you said, but you had tried some things, and you really wanted to be a tech entrepreneur, which was pretty cool back in the earlier times, like you were saying in 2005-2006. So maybe just share a little bit about what then prompted you to take on your current mission, which is storytelling, and what you call yourself today, which is the "master of first times." So can you share a little bit about that transition?



Ann Bernard:

Yeah, so that in itself, it's multiple timelines of making changes, and I feel like I've lived quite a few lifetimes already, because I have reinvented myself so many times. So I got to New Orleans, and eventually reached my breaking point, really being back in uniform. I'm always happy to be back amongst the Marines, but I always know that's not what I want to be doing. There's something in doing to the best of your ability, what you don't want to be doing, because it teaches you that you can give your all no matter how you feel, no matter what you think about it. So part of it is the grind, but some of it is like, "How do I still make a difference, even though I don't want to be here?" It makes you tough as far as your mindset goes.


But I get to my breaking point. And I saw two options at that time. One was suicide, like, ending it. And the other was, I don't know what the heck I'm doing with my life, and the one who knows is the one who created me and that's God. So I'm going to give my life to God. So having actually attempted suicide when I was younger, I knew that wasn't the answer. So I gave my life to God and a couple things, God brought me back to my family. You die to yourself and my identity was becoming an entrepreneur, was wanting to be that tech CEO, wanted to be a multi millionaire and ultimately making a difference in the world. But it was a lot more ego driven, now that I have perspective than at the time I was looking at it. So I had to let go and it took me two years to let go of my entrepreneurial identity. I would wake up at night, just stress and out of breath, and if I'm not this entrepreneur, if I'm not this driven, ambitious entrepreneur, then who's Ann Bernard? Then, who am I? I already knew the marine identity, I had shed that but the entrepreneur identity I had not.


The Marine Corps provided me an opportunity to go to Germany. So now I find myself in Germany, and I'm letting go of the entrepreneur, and I'm reconnecting with the fact that I love to travel, I love to explore. I'm traveling to all of these different countries, it's so easy to be in a new country over the weekend when you're living in Europe. So I'm in this new country, I'm like, "I'm visiting countries I've never been to, I should do something while I'm there that I've never done." So I started pursuing this journey of first times and new experiences, and my relationship with life completely shifted. It was like, "Oh, my God, life has so much to offer. There's so much to explore, there's so much to discover. This is making me feel so good. My moods are so much better. I'm learning faster and I'm engaging with living." So my time in Germany ended and back in the States, I'm like, "I can maintain this mindset." So I continued to travel, I did more, I started doing some writing. Something that happened as well, I came to understand that I don't communicate who I am, I don't share with others who I am. I don't open up with others who I am. I have a lot of Marine Corps friends, but that's a different type of friendship. We connect, because we're Marines. We'll do anything for each other, because we're Marines. Really doesn't really have anything to do with who you are as a person. "Hey, you're a Marine, I'm gonna take care of you, I got your back." So they never pushed me to open up and as a child, it's not something that I felt safe to do, so I didn't.


Now I'm realizing, nobody really knows me and I don't have connections and I want to change that. So now I started pushing myself to open up. One of the safe ways that I discovered to do that was through telling stories, because I'm having all these new experiences of travel all these countries, I have these all these stories from being a marine. Let me start telling those stories. I started sharing those stories. I was saying, "I'm traveling, I'm staying in Airbnbs, people open up their homes to me. So it makes sense that they have questions, they want to know more about me." So I told them stories, and their response and their engagement and how good it felt to start opening up was just incredible.


So, many things happen. I'm having discovery, different things happen. I haven't been working. I've been traveling for a couple of years, I'm getting to the point where I'm out of money again. So back to the Marine Corps, I go. And I found myself back in Okinawa, Japan, and back in Germany. My last go in Germany was really tough, because I really believed in what my job was, but a lot of people didn't care and it was very important. I poured so much of myself in it and it was exhausting for me because of how much I had to do to shift people around to see what they needed to do. Then at the same time, all the traveling had been incredible. I had grown and I had learned but I am an entrepreneur through and through. It's like I'm not making a difference in the world. That was leaving a hole. Now that I was whole, I had a hole because it was all about me. Now I was ready to return to being an entrepreneur in a more humbled way, in service of others like, "Whoa, what do I do?" I had been on this incredible journey that had changed me, a first time in new experiences. I'm like, "Let me bring that to other people." So I started 365 Firsts Challenge, which then brought me to...



Laurie Barkman:

What is that?



Ann Bernard:

So 365 Firsts Challenge -- there's an app now -- you make your list of things that you've never done before, but it's not a bucket list. I don't believe in bucket lists because the mindset behind the bucket list is like these are things before I die.



Laurie Barkman:

Yes.



Ann Bernard:

So the 365 Firsts Challenge is how to maximize what you get out of life today. What experience can you have that you've never had before? Or how can you elevate a goal? Something that you achieve, something different, a first time so that today is all that today can be. What I learned with some of your experiences is that there are so many incredible benefits. It improves your cognitive abilities and helps you be more open minded, creative, it can be leveraged to develop your confidence about your comfort zone, and face your fears. Everything that I always knew as a coach, all the experiences that I've had in my life, I brought them all together into this 365 Firsts Challenge. Then I moved to Las Vegas, because of all the cities around the world, Las Vegas is the one city associated with the first time you experience - first experience. So I created the app, and I'm ready to go. So this is the beginning of 2019, wait, 2020. Beginning of 2020.


[Laughs]



Laurie Barkman:

What year are we in?


[Laughs]


Ann Bernard:

Literally just looked at the corner of my computer.


I was raring to go, and then COVID hit. Let me backtrack a bit. One of the first things that I say is when I created the 365 Firsts Challenge, I started this podcast to share my first time stories, to inspire others to embrace first times and new experiences. When COVID hit, well, I always wanted to hear other people's stories so I started the First Time Storytelling podcasts and as people are coming on, some can tell stories, but the vast majority are not storytelling. They're teaching, they're sharing facts and information, but they're not storytelling so I created a free little webinar to teach people how to tell stories, and then that grew into a book, and then that grew into a course. Now, 23 February, we're gonna have our first virtual summit.


This can be bigger, this can be more, and then I grow it. So first time storytelling during COVID. Although during COVID, there're so many first time new experiences that you can have at home, but that shift took longer for people because I didn't account and that's on me. You're always learning, I didn't account for how long it would take people to adapt to their new circumstances of the lockdown of accepting the new reality that we found ourselves in. So I had shifted, nobody else had, so then I shifted again. Something else...I'm realizing I need to be a little bit more patient.



Laurie Barkman:

I was going to say some things just need time. So from a service perspective, how are you making money through 365 Firsts? Is that an app that people pay for?



Ann Bernard:

No. So for 365 Firsts, the way that the app is right now is very baseline. My vision is to help raise human potential and to do that through action-based self development. I've developed that platform into something that is going to help you drive yourself forward in all the things that you're trying to accomplish. I want to put machine learning AI in the platform. Because when you swipe on something that you've done -- you are the sum of your experiences -- so on all the things that you've done, paint a picture of who you are.


The baseline of self development, self improvement, and really anything, is self awareness. Unfortunately, the vast majority of people do not have high self awareness. Having the wrong impression of who we are sets us back. We can't go anywhere from that. We need those really strong baselines to grow from so that we can break our patterns. In the future, that platform, I want to develop that platform to do that.


One of the ways it's going to make money is that you're gonna swipe on the things that you want to do. I'll be able to provide the ability for you to buy the equipment that you need, or the tickets or whatever it is that you want to do right in the app. Then add the layer based on who you are, what you need for inspiration, for motivation to follow through. Lots of people are dreamers, and there are thinkers, but the way it happens is when you actually take the actions and you follow through. It's taking everything that I've learned in my lifetime, so far in that experience, and I want to bring into a platform that even though the platform is the same, but how you're going to interact with it, it's going to be different than me. Because we are all individuals, and we all need to be maximized differently.



Laurie Barkman:

Definitely, everyone's different. I love how you explain that. How you came into that vision and how you're bringing it to life. If there's someone listening that's thinking about their next and what their journey might be, what advice would you share for people facing transitions in their life or their career?



Ann Bernard:

Be excited about the transition, and do not beat yourself up because of where you happen to be. Like I said, that's something that I have to keep reminding myself because nothing ever moves at the pace that I wanted to. What I've come to realize is that it moves at the exact pace that it needs to. So 2020 happened, I had to change my plans, I had to pivot, things didn't work out. What happened in 2020, all of my old scripts, from all those years prior of being an entrepreneur and facing failure came back up. That allowed me to work through those scripts, so that I could rewrite and move forward.


If you're in a transition, it's not moving as fast, dig in. Try to find out what is happening, because your brain has had a certain experience in the past and it's leveraging that for the now. You might need to be thinking completely differently to go into the future. But if you're in a pause moment, it's a great time. That's what those moments are for, to have those realizations, to have the "Aha!" moments, to look back on your life, to look back on the timelines, look back at how you view things, and then create the shifts that you need to in order to move into the next phase.


My word for 2021 is ‘build’. Because as I look back in the last year and a half, it's been a lot of establishing foundation. I still need to do a little foundation work, but now that that's there, now I can build. Understand where you're at in this process, so that you can really enhance things as you move forward. Otherwise, you're gonna find yourself back. It's life. It's incredible, it's very magical when you do realize, 'Okay, I'm living my life in circles, because I'm not learning, I'm not changing, I'm not growing.' So if I want to stop doing that I have to change.



Laurie Barkman:

I like how you picked a word and the word you shared was build. I think if I was going to say a word it would be ‘evolve’. That's the one that's been on my mind quite a bit. That's great insight. I appreciate you sharing that, and I appreciate your sharing your story. Two final questions for you. I love to ask everybody that comes on the show. If you have a favorite quote, about entrepreneurship or leadership that you can share with us.



Ann Bernard:

I had to write it down. I have a really bad memory for quotes, but one of the ones that I say is "You don't know what you don't know. So don't beat yourself up for what you don't know." But another one that I really like is, "If you're going to doubt something, doubt your limits." That's by Greg Anderson. Being an entrepreneur, it is the toughest. I've been to boot camp OCS, have been deployed to Iraq, nothing compared to being an entrepreneur. It pushes me to my limits all the time. I've had enough life experience to know that I can always dig deeper. If you're going to doubt something then doubt your limits, because trust me, you have more to give, you have more to offer. There's more there for you to dig into and leverage.



Laurie Barkman:

Yeah, exactly. Keep pushing yourself and don't doubt yourself. If people want to connect with you, Ann, how do they find you online to learn more about you?



Ann Bernard:

One of the best places to find me these days -- because that's something else that happened, I focus on one platform -- it's YouTube. I'm actually running three channels. Y'all shouldn't be surprised by this by now.



Laurie Barkman:

[Laughs] You've got a lot going on.


Ann Bernard:

[Laughs] I'm reviving my personal channel, Ann Bernard, and then the other is 365 Firsts and the other is First Time Storytelling so it's all part of the 365 Firsts family. If you're interested in the storytelling, then that'd be the channel for you. You can learn more about storytelling and how to do it. Then the 365 Firsts is about the journey of first time and new experiences, but a lot of self development, trying to edge it. I'm aiming to take it one little piece, one sliver at a time, and teach people about self development. To include talking about finding your own solution. There's no one size fits all answer.



Laurie Barkman:

That's exciting. Awesome. Ann, thank you so much for coming on the show today. It was great to speak with you about your ‘what's next’ experience. I really appreciate it.



Ann Bernard:

Thank you very much for having me.



Laurie Barkman:

If you're an entrepreneur facing these challenges. I get it. I work with businesses from small to big for strategic planning with your team to achieve your vision.


Visit smalldotbig.com to schedule a call with me. I'd love to connect with you. Be sure to catch the next Succession Stories episode with more insights for next generation entrepreneurs.


Thanks for listening.




Click here to book a strategy consult with Laurie Barkman

SmallDotBig is a strategic advisory firm for owners of small to mid-size companies. Our mission is to dramatically increase the value of your business anticipating a sale or ownership transition in the future. We help you get more freedom over your time and more happiness in your personal life. Our process combines Value Building, Executive Coaching, and Strategic Planning. Want a business and personal roadmap to achieve your dreams?  Reach out today. 

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