#28 Understanding our Voices and our Ambitions

Today's Guest: Gary Wilkin

Today, I interview Gary Wilkin who had such a strong background in technology, that his skill set was being able to speak to clients and find out what their needs are, and then return to the tech side and translate that message to that team, and vice versa.

As a leader and liaison, he learned to use very clear, established vocabulary, and he also became an excellent listener. As time passed, his value grew so intensely that certain projects would be helplessly doomed without his help. So, even though he had lost interest in the work itself, he felt stuck there because his role was so valuable.

He reached his ceiling and made a conscious decision to move on and do something new and different. Gary likes to say that every transition has three parts: a beginning, a messy middle, and an ending. His experiences transformed his outlook on his life.

Now Gary uses his expertise to coach people through visualizing a future they never thought possible. He helps them to make plans to get there, as well as to re-frame the way they think about their lives and roles in this world. Download the Stronger Action Guide, a free booklet by Tom Ziglar: myretirementmission.com


Gary is a licensed Ziglar Choose to Win and See You At the Top coach. He specializes in helping seasoned professionals transform their lives from “I have to” to the life of “I want to”.

Gary combines the life experiences gained in a four-decade career in technology across a variety of wide variety of environments with powerful conversations to help his clients transform their lives one simple choice at a time.

Connect with Gary here:

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Transcript of Interview

Find Your Voice, Change Your Life Podcast 

Podcast Host: Dr. Doreen Downing

Free Guide to Fearless Speaking: Doreen7steps.com

Episode #28 Gary Wilkin

“Understanding Our Voices and Our Ambitions”


(00:36) Dr. Doreen Downing:

Hi, this is Dr. Doreen Downing and I’m with the Find Your Voice, Change Your Life podcast. And every week I get to interview somebody who has a story. It’s a story about how either they had a voice and lost it or they never had it in the first place. And they found it. So, it depends on who we get to listen to what the story turns out to be. So, stay tuned today. But before I introduce Gary Wilkin, I’d like to say thank you to everybody who’s gone to Apple podcast, and then a review. I have so many now close to 20. And I’m excited. And I just learned this week that we have 500 downloads. So that means you guys are listening. And I’m happy that you’re here today. Today, we have Gary Wilkin, who is a licensed Ziglar Choose to Win and See You At the Top coach. He specializes in helping seasoned professionals transform their lives from “I have to” to the life of “I want to”. Gary combines the life experiences gained in a four-decade career in technology across a variety of wide variety of environments with powerful conversations to help his clients transform their lives one simple choice at a time. Oh, Gary, that sounds so fascinating. I’m really looking forward to today. Thank you for being here.


(02:12) Gary Wilkin:

Well, thank you so much for having me and giving me an opportunity to share. So, this will be, this will be very, very fun. I’m looking forward to it.


(02:19) Dr. Doreen Downing:

Yes, that’s partly what we do here is to create an environment so that people step in. And it’s not about stepping into pain, but it’s into sharing perhaps some pain that you’ve had in the past. But it is– we get to do it together, we get to go on this inner journey. So that’s where we like to start is so you– I do know that you did have a voice but you lost it. Can you open up the story about what that was all about for us?


(02:52) Gary Wilkin:

Well, the four-decades career in technology– I had to get my calculator up to make sure that’s how long it was– and early on, things were much different than they are today as far as the computing environment and the types of problems we solve. But even from an early stage, amongst the technical folks, I was the one they would always send out of the room to go talk to the business users, those evil people that made us do all these crazy things. And I was the one that could go and talk to people and then come back and translate that into the technology verbiage that they understood and could help create the solutions. And so early on, I was the communicator and that became my strength of being able to talk. We laughed, it was bilingual, I speak business, and I speak tech. And so, over the years, that was my strength. And that was my voice because I understood the power of questions, to find out what we really need, the problems we really needed to solve, and not just what a symptom was or what somebody thought they needed. But to find out what the real issues were, and then come back to my technology team and explain the issues and then go back and forth with them to make sure that they understood.


(04:23) Dr. Doreen Downing:

Yes, I get that it was not only the power of questions, but the power of listening and knowing what the language is so that you could speak both languages, but you had to listen first.


(04:35) Gary Wilkin:

Right. And we have to spend a lot of time establishing vocabulary. Because in large meetings if we’re trying to describe a concept if we don’t come up with a clear definition, who spent half our meetings going, “well you know this one thing that looks like this, that we’re doing this,” “oh no, that other thing is that what you mean…” and I found that, you know again, being very clear. Establishing a common vocabulary just allowed communication to flow even that much better.


(05:06) Dr. Doreen Downing:

I would say that “thingy” is one of my, is one in my language. “Oh, yeah, that thingy that goes in the other thingy.” So, I understand that. So, what a valuable key role you played for the technology people to be able to come back and also help solve problems that the businesspeople needed. So yes, so you, you have this special “King Gary” role to play and the messenger that went out in both directions, but something happened.


(05:43) Gary Wilkin:

And so, this, this went on. And as I matured in my career, you know, towards the last few years, there was a slight shift in that I was my, the sounds weird, but my success harmed me, in that I was becoming viable on a couple of projects that it wouldn’t let me off, because I had become integral in that. And that may sound conceited. But that’s not what it’s intended. But I became valuable. And I was, I was held on a couple projects, I needed to stay put rather than going off to the next greatest new shiny object. And so, I started to feel as I was losing some relevance, my contribution wasn’t quite as aligned to the corporate mission that I wanted. And I started to feel as if I was losing my voice, because my voice was all about the meaning and the purpose of the projects and the problems we were solving. And so that that started to kind of take its toll. And at one point, and I think it was a snowy November evening and 2018, or actually morning, and I was going to have to go downtown, it’s going to take a couple hours because of the weather. I was looking myself in the mirror and I said, “Do you really want to do this, or not just the not just the meeting, but keep doing this?” I thought for a second and I said “No.” And then it hit me, “then what?” And so that began that transition of having a strong voice to having a little bit weaker voice and on call it massively weaker to now, no voice, because it wasn’t that it wasn’t like I didn’t have my voice, I didn’t have a message. And I think that’s the shift now that we talk about is, if you don’t have a message, it doesn’t make a difference how big your voice is if you don’t have anything to say and you don’t have anything to share. And so that was quite a tumultuous transition. But that was the best part of the transition was agreeing that I needed to stop. Every transition has three parts: an ending, a messy middle, and a beginning.


(08:10) Dr. Doreen Downing:

Ooh, I like that, say that one more time.


(08:13) Gary Wilkin:

Okay, every transition has three parts—and I have to I have to attribute this to Dr. Bridges. In his book Transitions, it was a great book– every transition has three parts: an ending, where you have to come to grips with what is actually stopping; then you have the messy middle, which is the fun part of try this, try this, try this, you know different things. And then once you settle in on something, then you have the new beginning. And so messy middles can take a long time or a short time, it just depends. And unfortunately, we tend to, as– I’ll speak for myself– as type-A type people, we want that messy middle over. We don’t want, you know, any uncertainty or doubt or that type of stuff. But I took my time to work through that. And so, I, you know, so I said that November 2018 is I’m not going to do this anymore. I started studying and whatever. We did the numbers and five months later, we sold our house, bought a house, and moved across cross country. And that intervening time, I don’t remember much. I’m so glad because selling a house and moving across the country is a big deal. But so, I’ve made that transition out of the corporate environment. But I’ve still not, quote unquote, “retired”—I’ll talk about “retired” in a minute. But I tried some things that I thought I would enjoy, and I didn’t and I kept looking at and I step back and say from my studies, what am I good at? And I stepped back and abstracted, “what was I always good at?” I was good at asking questions. I was good at listening. I was good at understanding how to find out the real issues. And in the generic term was a coach. And so, I started to figure out, what does that look like for me? And how can I serve people with that. And I started to, you know, read about that and do some different things. But it wasn’t until I started to build out my focus on helping people retire like I did. Okay, I’m going to leave corporate, I’m going to do something else, here we go. And, but I realized that we don’t retire anymore. You know, you know, it’s not like my dad, he worked for the phone company for 37 years, he got his gold watch, and he went home. And we don’t do that anymore. And so, I started to reframe that. But the same, the whole time, my whole theme was, understand what you want to do, understand what tools you have, and then how can you make it happen? What, how do you impact change? Well, I started to work that, but then I found the, the Ziglar coaching system. I’ve been a fan of Zig Ziglar for decades, and, and worked in with that. And they’re all about the very same things: understanding why, and why you’re doing things. And that opens up your “what” and your “how”. And so, I started looking at that, and saying, Why am I here? What, what was I looking for, and my career has shifted into early days, as I want to do this, I want to do this, I want to do this. And it’s slowly, ever so slowly shifted to I have to do this, I have to do this, you know, I’m sure there’s many folks out there listening to this, that we’re still working or because I have to do because I need medical coverage, or I have to do it because I need this, or whatever. And I found that we can move from “I have to” to “I want to”, we’re going to stay in place, we can go someplace else, whatever. But we it’s a mindset shift that allows us to reframe where we are and what we’re doing to, to take those, “I have to”s, reframe them, or change the environment and turn it more into a life of a want. And that’s a fabulous transformation to both experience and to encourage and come alongside and guide others to do that same thing.


(12:39) Dr. Doreen Downing:

Yes, I’m going to want to ask you a few more questions about that in a minute. But this whole when we first started today, and I introduced you the going from I have to to I want to and then your story about having been in an environment where you’re doing lots of translations. I mean, you’re using your voice, in fact, but people are saying, oh, he’s got a voice, but it’s not your voice. You were translating the business language into technical language, but it really wasn’t a message that you were meant to be here on earth to give. And somehow that moment when you looked into the mirror– and I’m thinking that a lot of people have those wake up mirrors– luckily it sounds like you didn’t have like a heart attack or some kind of accident. You know, a lot of people talk about having had an accident that then woke them up and they said, “Gee, I can’t do this anymore.” So, I’m glad that that happened that I was looking yourself in the mirror and confronting truth and oh, wow, seeing truth come back at you with the “I don’t want to.” And then “what else?” So that that moment, “but what else”, and then your explanation of the transition and being in the messy for a while, in the “middle messy” for sounds like some time. But what I also want to say is that I hear in the “well, what am I good at?” I loved hearing you ask that question. And that’s something I think listeners need to do is “what am I good at? If I’m looking for my message, what is that?” And then your original, “hey, I’m going to go one place and listen, and then I’m going to translate it and put it in another place” feels like well, you applied that to yourself in a way, like what is it that I want and I need to translate it and then I need to make it better. So that seems like a pattern that you did earlier in life and you’re only doing it now in a more personal way.


(14:55) Gary Wilkin:

Yeah, that’s an interesting observation as you were saying that back, my strong voice early on– I never thought of it as merely a translation– so it was it was a strong skill. And so, it was a skill that I knew that I could execute but and I would try to bring my insights into things on you know, impact the solution and that kind of stuff. But you’re right. now it’s the time of in one work I’m still doing a little bit of translation, but it’s more of in the form of question. So, as I work with people, I’m drawing that out of them. And so, they are, they’re sharing their, that’s their message there.


(15:40) Dr. Doreen Downing:

Oh, I love it. I love what you just said, because in a way you’re going to people and asking them the questions. And you’re listening, right, as you’re using that skill you had way long time ago, only you’re doing it for—what– the benefit of those of us out there that need to be listened in to actualize ourselves. So, let’s move into what exactly you are doing. Unless you had something else you were going to say right there.


(16:05) Gary Wilkin:

So, what, what I’m doing right now I would have to characterize as the greatest time in my life, and I am having the opportunity to sit down with people and ask them some questions and listen to them and draw them out. And one of the most fun opportunities I have is to do what do we call a vision exercise. So, think about where we meet two years from now, three years from now. And I haven’t seen you and you, I run up to you and say, “Hey, how you doing” And you get to sit there. And I want you to think about what you have a dream to do. And imagine that anything is possible. And we talk and I start to love what it is three years from now you’d like to run it together? What would you like, like to be able to tell me about what’s your life been link? And, you know, at first it’s, you know, it’s like, deer in the headlights. We don’t get asked that question very often. But when you encourage people to not okay, because first of all, we people tend to dream about what they think is possible. And I said, “No, no, everything is possible, we are what we want to do”, and then seeing people light up. Because there’s been years and years since I’ve been able to dream. You know, it’s almost harkening back to what else did you want to do when you wanted to be an astronaut? And, and getting back to that? And so, taking people into, into that place of “what could I, what would I do if I could do anything?” And then then we step back and say, why not? Let’s take a look at it. And so the heart of the transformations that I am able to be a part of this, this awakening of “what’s, what am I meant to be? What’s my why, and then how do we achieve that?” And that’s to me is like I said, Is this just the best time in my life that I’ve ever had.


(18:11) Dr. Doreen Downing:

Yes, the people who are listening, I just want to reflect back that Gary’s face is so lit up, and he’s smiling. And it’s just beautiful to watch his joy as he talks about what he does. So, I’m saying that out loud, because people can’t see if they’re listening they can’t see. And what I also notice about what you’re saying is that it’s not about what is your goal? Sometimes goals feel like, Oh, you know, like climbing a mountain. what you just did you know, is what is your dream? And what is your vision and it just felt like, the universe opened up and there’s just so much more expansiveness, then I got to make it one step at a time to the top of the mountain. That’s, that’s my goal to get to the top, rather than, Ooh, what’s my dream? And it just feels so much more creative.


(19:08) Gary Wilkin:

You know, and the fun part is when we have that vision, you have that dream you still have to take steps but that’s not the emphasis. There’s like, it’s like hurdlers track and field. When they’re running up to the hurdle, they’re not looking at the top of the hurdle, or they’re looking, you know, several feet beyond that. If they looked at the hurdle, they will be tripping over it. And so, as we’re looking at our vision, we’re looking at that goal down, not using the word goal, we’re looking at our dream and looking at our vision. And these bumps along the way are there, but we’re so focused on that dream, we can keep moving through, keep moving through. We have the strength and persistence to keep going through those.


(19:55) Dr. Doreen Downing:

The motivation. Yes. You know, it’s like it’s drawing us as opposed to us really plowing our way through to it so… Well, Gary, we’re getting near the end of time. And I want to see if there’s anything else you want to say about what you do, how we find you how people can look you up.


(20:17) Gary Wilkin:

Well, there’s two simple ways. If you’re on LinkedIn, just look for Gary Wilkin spell my name out, we’ll have links at the bottom of this W-I-L-K-I-N. There I am. My company name is My Retirement Mission. Now when I started that I was thinking “retirement” and now I would like to change it to retirement 2.0. Retirement 2.0 is retiring from a “half to” to “I want to” and you know, and so that’s it. So if you go– I haven’t changed the name– but it’s still MYRETIREMENTMISSION.COM . But my goal is to help you go from I have to, I want to. And I’ve got a booklet there that you can you can download. It’s actually by Tom Ziglar, the CEO of Ziglar Corp, it’s called Stronger. And the whole concept of stronger is that even now we’re still in the effects of COVID-19, they’re going to go on a little bit longer than I think we all hope that they’re still there. And so how do we make it through this, these tough times, so we need to have the right mindset, you know, the stronger mindset says, “we can go through, there is hope. It’s based on “we have hope.” And there’s something we can all do together to grow through this stronger. And so that is a book that I would really love to share for you just to take through. It has a worksheet in it to help you kind of work through this mindset. And once we have the mindset growing through and growing stronger, we can take on and that’s the thing I would love for you to come up and upload and take a look around.


(22:03) Dr. Doreen Downing:

Great, I’m sure people will because we all have the need right now to have that particular kind of mindset to grow stronger, as opposed to anything less than that. And I appreciate you offering that to us. Thank you. Any last word, Gary?


(22:25) Gary Wilkin:

I think that the thing that, that one thing to remember is that we have the power to choose. Our future is based on our choices today. And so, the power to go from “I have to” to I want to is a power of choice. And that choice is total—the power is totally an influence. And that’s the thing. We have what we need to choose.


(22:54) Dr. Doreen Downing:

Mm-hmm. As you said in the beginning where I said the beginning, “transform our lives one simple choice at a time.” Thank you, Gary.


(23:02) Gary Wilkin:

Well, thank you, Doreen.

Also listen on…

7 STEP GUIDE TO FEARLESS SPEAKINGPodcast host, Dr. Doreen Downing, helps people find their voice so they can overcome anxiety, be confident, and speak without fear.

Get started now on your journey to your authentic voice by downloading my Free 7 Step Guide to Fearless Speakingdoreen7steps.com.

7 STEP GUIDE TO FEARLESS SPEAKINGPodcast host, Dr. Doreen Downing, helps people find their voice so they can overcome anxiety, be confident, and speak without fear.

Get started now on your journey to your authentic voice by downloading my Free 7 Step Guide to Fearless Speakingdoreen7steps.com.