Category Archives: Real Life

Lessons of the Year

A few years back I wrote a short article for my birthday that shared 36 things I’d learned in my 36th year. I’m going to go a little bit deeper for my birthday this year and share a couple of things that really stuck with me this year.

The last few years before this one were what I consider years of consolidation for me. I was focused more inwards than outwards, finishing my education and learning the lessons of a first time dad. This year was very different. I was standing alone for the first time in a long time and I was surprised to once again the energy that comes from knowing that there is no one to blame but yourself if you aren’t getting what you want out of life.

This was a year of expansive growth. A few weeks after my birthday last year I elected to change jobs and companies after 17 years of growth in one place. I moved from the world of insurance to the world of staffing effectively. This change effectively sacrificed the expertise I had built up related to the insurance industry. At my new company I was no longer able to deliver value as a SME. My success was totally dependent on my ability to learn, adapt and generate results through my personal mix of personality and experience. It was exciting to say the least.Trivial Warfare

A couple of months later I started Trivial Warfare, the podcast that defined much of my year. Along with my best friend Chris I committed to recording, editing and producing a weekly trivia show. I didn’t worry much about how successful it would be. Instead I enjoyed the chance to share something that I love with people. As the year moved forward the type A personality that I try to keep hidden behind the scenes took over and pushed me to learn the craft so that we had a chance to be as good as we could be.

I ended up going to a couple of conferences, meeting a ton of great people and stretching myself in ways that I didn’t realize I could stretch. Sitting here now I easily self-identify as a podcaster even though it’s not my source of income. I’ve gotten so much out of it that it would be silly to pretend otherwise.

With that in mind, here are the four biggest lessons that I’ve learned and experienced personally this year.

The Numbers Game

Life and success really do boil down to a numbers game. I was at New Media Expo in Las Vegas back in April when I heard for the first time. It was part of a presentation by Jordan Harbinger from The Art of Charm. He was talking about how much failure is a part of success and challenged us to determine if were willing to fail and fail again in order to succeed. I’ve heard variations on this theme before but it was different this time. I was in a place where I could apply it quickly and I did. I introduced myself to over 200 different people in that short period of time. Here we are 6 months later there are around 5 people that I keep in touch with and 2 or 3 that have become really good friends. Was it worth going through 200 uncomfortable situations to make 2 or 3 good friends? Absolutely.

People Are Waiting For You

Claire Danielle Carol RR JP MAI’ve described the podcasting community to people as a group of friends that have been waiting to meet you. That’s exactly how it has felt. Don’t get me wrong. I’m not saying that everything is unicorns and rainbows. But what I found as I extended myself and merged with this existing community is that there were people there for me. It’s not going to be everybody, it might not even be a big group. But if you extend yourself and put yourself out there you will find your tribe. In fact, you might be the glue that brings the tribe together. It really makes me wonder how many great friends I’ve missed out on over the course of my life because I didn’t make it a point to engage. Now, as I look forward to my 3rd conference this year in a couple of weeks I know that I already have friends waiting for me. Both the group that I already know and the ones I haven’t met yet.

It’s About Action

Both of the previous points are dependent on this one. They only way they work is to get out and do things. It’s important for the introvert in me to point out that this doesn’t mean doing things alone. It means engaging in things that are bigger than you are and finding out what you have in common with people who are engaged in the same thing. It is easy and safe to live a quiet, personal life. You can live your whole life like that and not bother anybody. But if you want to do something special, if you want to achieve something great then you’ve got to be willing to sacrifice your safety and comfort and get out to do something. This activity will make you eligible for all the amazing things that only happen to people are willing to truly live life rather than sit back and watch the time go by.

Sometimes You Have to go the Wrong Way

This is the most recent lesson that I learned this year and I want to be sure that it sticks with me. I was trying to drop off my rental car at the airport in Toronto the other day. I didn’t look at the map but I knew generally where I needed to be. I got in the area and drove right past the garage where I needed to be. There was no way to turn it. I backtracked to see if I missed it. Nope. I circled the entire area and still couldn’t find a way in. I wasted an hour trying to find my way in.

Oddly enough, there were signs that showed the way to go, but the stupid things all pointed away from the airport. They were obviously wrong so I ignored them. Eventually in frustration and anger I decided to follow the signs just to prove how stupid they were so I could get back to searching for a way in. The sign put me on a road heading in the opposite direction of where I needed to go. And then about a half mile out the road looped and turned back in on itself. It was the way in.

I thought I knew better than the signs that were pointing in what looked to be the wrong direction. But I didn’t have all of the information that I needed to succeed. Life is like that sometimes and my close friends know that I’m hard-headed just like that most of the time. It’s good to remind myself that I don’t know everything and that sometimes I just need to follow the signs no matter how wrong they look.

Be blessed in 2016



Relay For Life

It’s been a while since I wrote a real Bootstraps post. I stopped writing regularly back in 2012 after starting my MBA. The workload was just too much for me. I welcomed my son into the world in 2013 and then graduated in 2014 (Yay Me!). Soon after that I was changing jobs, separating from my wife and starting the podcast that I’d had on my mind for a couple of years ( if you haven’t checked it out yet).

Most of my free time now is dedicated to the show. The recording, editing, marketing and what not is enough to keep anybody busy. Still, I have a soft spot in my heart for Bootstraps. It represents a lot of firsts for me. It was my first attempt at building something, at attracting an audience, and at writing regularly. I’m still proud of it, but don’t figure that I’ll be posting a lot of articles to it in the future, particularly because I can write about them or talk about them on Trivial Warfare.

Still, every once in a while something happens that just doesn’t fit what I’m doing on the other show. That’s what happened this weekend and I want to share it with you because it really touched my heart and reminded me of an old lesson. Read the rest of this entry

Farewell Florida Blue

Last Tuesday I made another one of those decisions that will alter the course of my life. I’m leaving Florida Blue after 16+ years and moving to another great company named Adecco. This amount of change in such a short time is unprecedented for me and I find myself doing a lot of thinking about the past and what I’ll be leaving behind. The decision to leave Florida Blue was especially difficult. It is a great company. It cares about its employees and it treats them well. It also cares deeply about its customers and makes it easy to buy in to its mission by going out of its way to ensure that customers come first.

It’s much harder to leave a company when you believe in it and when you trust and appreciate the people that you work with. It’s also very hard to leave anywhere that you’ve spent as much time as I’ve spent at Florida Blue. I find myself deep in thought as I walk out of the parking lot each day, taking in the scenery and realizing that I will only make that walk a few more times in my life.

I grew up at Florida Blue. I started when I was 21 and was no more than a boy. I learned how to be a man there. I learned about responsibility and work ethic. I learned about the dangers of assuming you know more than everyone else and I learned how to get along with people. I learned so much about getting results in all kinds of different situations. I learned how business works, I learned the basics of sales and I learned how data moves behind the scenes and how to get things done in the IT world. The people that have worked closely with me can vouch that Florida Blue got its money’s worth from me. But what I find myself focusing on now as I try to transition my work is just how much I got from the company.

My father worked at Florida Blue for years before I arrived. That means I was being supported by the company before I even worked there. I met my best friend and my wife there along with countless other friends and outstanding relationships that I treasure today. Florida Blue gave me the opportunity to finish my education. It also gave me the opportunities to grow into my own as a leader, making decisions and living with and learning from the consequences. I can’t say enough good things about the company as a whole.

The question that I get the most is also the most obvious, why leave? Obviously it wasn’t an easy decision. The money had to be right of course, but it’s bigger than that. I owe it to myself at this point in my career to stretch my horizons. Much of my knowledge is institutionalized at this point. My first year at another good company will introduce me to countless differences that will help to shift and balance my experience. This will round out my experience nicely and has the potential to help me grow exponentially. I love Florida Blue. I think it’s one of the best companies in the country, but I know that if I remain there for my entire career that I will prevent myself from maximizing my potential due to the homogenous nature my experience.

And so I find myself saying goodbye to so many familiar sights and people. It’s not the first time that I’ve initiated an unexpected change in the direction of my career, but it is definitely the most difficult. I want to say thank you to all of the people that I worked with over the last 16 years. Thank you for your patience, your kindness and for all of the lessons that you have taught me. I have loved working with you and I will miss you dearly.

Jonathan Oakes

Paying It Backward

I was at home doing my homework on a recent Saturday when I was struck by inspiration. I can say with certainty that the resulting idea is one of the best I’ve ever come up with. I know this to be true because of the great potential for it has for making people happy and the utter lack of self-gratification that it involves. Most of the rest of this blog talks about how the idea came to me, if you want to skip straight to the idea feel free to jump down to the last couple of paragraphs. But first, let me encourage you to share this message via your choice of social media sites. I’ve never asked anyone to share an article before and I probably won’t ever do it again. But I believe that we can make the world a little bit brighter if this message gets out to enough people. Read the rest of this entry

Elementary School Shooting


It is another horrible day driven mercilessly into our collective memory. Today Adam Lanza, a 20-year old sociopath, killed his mother and then went to the school where she was a kindergarten teacher and opened fire on teachers and students, killing 27.

It’s hard to process a tragedy of this magnitude. The first emotion I feel is anger. I have to admit, I hold onto that anger. It’s a much easier emotion to deal with that the pure sadness that will follow. I put myself in the shoes of the parents who dropped their children off at school today who will never see them alive again. Such anger, I wish the shooter was still alive so the parents could take their pound of flesh directly from his hide.

I can’t help but try figure out why a person would do something like this. It’s just the way that my mind works. Earlier today I heard an incorrect report that the shooter was a father on a student. I immediately wondered if this was some sort of vengeance for extreme bullying. But that’s not the case. This wasn’t logical. This wasn’t something that makes sense. This person shot his mother and killed her. But this wasn’t enough for him. He followed this up by going to her workplace to kill her students.

I know what I think it was. The fact of the matter is that angels and demons both exist. They aren’t fictional representations of good and evil. They are beings of spirit that drive us and influence us to the extent that we allow it. Was Adam Lanza crazy? Of course he was crazy. What we don’t know is why he was crazy. I suppose that’s a different question for a different day.

For now we have a couple of options. Some of us will cry and mourn and others of us will rage. As for me, I will rage.

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