30 Days, 30 Episodes: Day 2 - My Journey of Career Shift and Self-Realization

I'm Matt Gilhooly and this is the Life Shift Candid conversations about the pivotal moments that have changed lives forever. Hello, everyone. I am back. This is day two of this month of posting a bonus episode every every day for November.

So we are on November 2nd, and I'm already wondering if I am going to be able to do this for all 30 days in November, but we'll find out. And so I don't have a big plan going into it. I did ask a little AI chat GPT for some suggestions of things that I can cover for each of these.

But I will also ask you, if you're listening and you want to give a question that I can answer on one of these episodes, please send me a message on Instagram or send me an email mat the life shift podcast.com and I will get that and hopefully answer that, obviously, if I can. So today's suggested question is to discuss some key lessons from my career journey.

All right, so I talk about this a lot in a lot of these episodes about how for so much of my life after my mom died, I kind of just absorbed what I was supposed to do or what I thought everyone else wanted me to do or I guess society required of me to do. So that was like, get good grades, get into a college, get a scholarship, get good grades, graduate, go to get a master's degree, get a good job.

All these things that I was supposed to do.

So I feel like for so much of my life, especially early on, I wasn't really making decisions based on what I wanted to do or based on what I found interesting, but rather I chose things that I found easy and easy in the sense that I could do them well and then I could reach the next level of success, whatever that looks like, the next check mark, is that a promotion, is that more money, whatever it might be, or I would do well and have something steady. So there were a lot of things that went along with that. So like after college I was like, oh God, what do I do? How am I going to get a job?

What am I going to do? That is something better than working in a mall, which is what I did during college.

So instead of getting a job, I was offered from the University of Central Florida. They were starting a one year master's program, a MBA program. It was actually 10 months and they offered it to me for next to nothing.

They needed good students to come in so that they could boost up this brand new program that does not exist anymore. So it wasn't a good idea. To begin with, but anyway, so during this program, it was again, 10 months, and I had to.

Or we all had to work 600 internship hours.

So I was able to secure an internship through a entrepreneurship grant, which then made me a UCF employee, which then made my degree program essentially free, which was super awesome. At 22, 23, postponing life, getting an MBA, checking all the boxes for me, and for what everyone wanted me to do.

So then I fell into entrepreneurship, essentially, like, working for small companies, doing a lot of things, which was good for me because I was learning different areas. I was figuring out what I was good at, what I was not good at.

I was becoming kind of that jack of all trades, which sounds good on the surface, but then it made me, like, just good at a bunch of things, but not, like, great at something, you know, you can think of like an accountant. You know what they do. They know what they do. They're really good at that.

A lawyer, you know, there's a certain area that they focus on, and they're really good at that. I was just, like, good at a bunch of business things, which is cool, but it's easily a place where we get bored.

So I worked for a couple small startup companies, and then I moved back to Boston to be closer to my father and my grandmother and to spend more time with my grandmother. And I was there for about 18 months. I worked for a. Another small company.

I mean, they were a successful company and I was in charge of operations, so I did a lot of stuff, but I was really bored, and I was kind of missing the South, I guess. I was missing parking lots if we're going to be real.

I lived closer to Boston, so we had to park on the street or in narrow driveways, and we had to deal with, you know, storms and snow and things that aren't that exciting. So I came back to Florida, and I didn't know what I was going to do, so I just applied to a local college here in Orlando.

And I had never taught before, and I didn't really, like, I wasn't a big finance guy, but they hired me to teach a finance class, so I taught that. And then about nine months, 10 months into that journey, I was promoted to the first department chair for this particular degree program.

And then I started building processes and training other people and hiring people, and. And then they started getting promoted. And then we had an additional few department chairs, and I had to train them.

And I just kept kind of moving through and just doing more. And then when things get a Little bit boring. I get pulled into a project and then a job gets created for me, which is really cool.

It was a director level. I was, like, really excited about it, a little nervous. But also they created this role for me. So I was like, okay.

So I was doing really amazing stuff, working with team that had been moved around a bunch of times. And this is really, like, I would say, like a pivotal moment in my life, this, this part of my life, as far as my career goes.

And it coincides along with my grandmother's passing. But during this period, I was transforming this department. I was creating curriculum for the first semester for all undergraduate students.

And, like, things felt really good. Like, things.

We were meeting certain criteria, but there was one person who I refer to sometimes as a bulldozer because this particular person had power and they had power to just wipe out anything that I had done.

And I felt like I was on this, like, target, like someone was throwing darts at me all the time because I would make like these 10 steps forward and then I get kicked back because this person would just erase it and change things.

Or at one point something changed dramatically that I was in charge of, which was going to change how many of my existing team was actually allowed to teach the class that was assigned to them. And I was not brought into the conversation until the very end. Everyone else knew I was just excluded from that meeting.

And it's like me, I'm like, trying to do all these things. I thought I was a good employee, but it was really not about me. It was about this other person.

And this person really kind of like, ruined my psyche and my ability to kind of move forward in my career in so many ways because I started doubting myself. I would go to work and then it would be 5:00, I would go home.

And the only thing I wanted to do was go to bed so that I didn't have to be awake, so I didn't think about work. And then I would have to wake up and do the same thing over and over and over again at the same time.

Towards the end of this, my grandmother was getting worse with her cancer diagnosis. And things were kind of progressing to the point where it was close to the end.

And so I put my focus there and I spent, spent, you know, the last 96 hours of her life with her in hospice. I had a most beautiful conversation a couple months before that with her. You probably heard me say it in a bunch of different episodes.

But during that time, I didn't really think about work. After she passed I came back and I said, hey, everyone, I'm going to take the FMLA leave.

I'm going to leave for 10 weeks and I'm just going to focus on grief. I'm going to focus on me. I'm going to do the things.

Did found myself, kind of realized that things don't really matter that much and I don't need to keep checking these boxes, that everyone kind of, or I assumed everyone wanted me to check these boxes. And so I came back and I asked for a demotion. Mid 30s asking for a demotion.

I got it, which was nice because they knew that I was a good employee and I was good at what I was doing, and they wanted to respect that.

And then they put me in a different role and it felt like, weird, but good because I felt like I took control and I hated part of it because I realized that that one person, bulldozer was the reason that I did that. And. And that person made me feel less than. And I don't think most of it was about me. I think it was about this particular person.

But that lesson taught me that I can stand up for myself and I don't have to follow the quote, unquote, traditional trajectory that people have for careers.

So after that, moved to Colorado, had a little sabbatical, enjoyed my time out there, came back, got a job that I hated, worked there for three months. I didn't feel great in that environment.

So again, I left the job without having any kind of backup, and I took five months off and I was able to travel and.

And kind of went to Thailand with a friend that wasn't really, like, we weren't great friends before, and we went to Thailand for 10, 11 days, and we got to be great friends, and now we're great friends. She's on episode four. Her name is Adrian, and we had a great time.

And I just kind of found this space in which I can make these choices, and they don't have to be what everyone expects of me. As long as I can pay my bill, as long as I feel okay, I can move forward. So, you know, that led into other things, got lazy.

Certain things like that happened.

But Emily, my friend Emily was like, maybe you should talk a little bit of why you leaned into fear and why this podcast exists and why you're doing these things. Well, it all kind of turned into this master's degree program during the Pandemic, where I was like, I don't know what I'm going to do.

I'm kind of bored. So I chose something that scared me. Every semester.

I chose a class that scared me because I wanted to be uncomfortable, to prove to myself that even if I didn't get an A plus, it was okay. I did end up getting a 4.0 in the degree program, but at the same time, there were classes that were just frightening to me.

Like, I didn't understand them going in, which always before, in the earlier version of my life, I would always pick the things that I knew I could do well. And this time I moved in, I was like, okay, I don't know what I'm doing, and that's okay. And it turned out fine.

And then I was able to kind of transition into leaving higher education. And now I work in a marketing department, and I'm the main content writer. And now I'm producing some podcasts for the company that I work for.

And every. Everything is brand new every time I do it. And I'm learning so much. It's only been about eight months, maybe.

And I can't believe, if I look back to when I started in March, all the things that I've done and all the things that I doubted on days one through, I don't know, 120, something like that, and how a lot of things become common practice. I'm learning, I'm still making mistakes. And. And guess what? It's okay, because we're not perfect. We're not saving lives, and. And that's okay.

And so it's been a really long jo of this career path of kind of following the next easiest thing, but also at the same time, what everyone expected me to do, because I was always just chasing, like, what can I do better so that I can get a better job, or I can tell other people in my life that I got a promotion or I got more money or whatever it may be, and they can celebrate me, and then I just move on to the next thing. Not so healthy. So now I'm doing things that scare me, like these 30 days of an episode every day.

So this is episode two of 30 Days of a Daily Episode. And maybe get a little bit of my journey. If you know me, then you know the story of bulldozer. And you know who I'm talking about.

If you don't know me, you probably know a bulldozer in your life. And don't let them do it. Don't let them break your psyche.

Make the decisions that make sense for you, not what you think everyone else wants you to do. So if it means asking for a demotion, if it means quitting your job to find something else else, knowing full well that you can then do it.

Follow what you believe in yourself that's going to make you happy or keep you from being unhappy, and you'll eventually find a space in which you're making those decisions for yourself. Hopefully you don't have to deal with this, and you've always been making those decisions.

But if you're someone like me that had to fight that and had to fight against it, and now finally find the space where things make sense again, I hope that you take this to heart. So that's it for November 2nd. I will see you tomorrow for November 3rd, and I don't know what I'm going to talk about, so we'll see you then.

And thank you for listening. And hopefully you'll stick around till the end of the month. For more information, please visit www.thelifeshiftpodcast.com.