Sitting on a mountain with sweat on my brow, I was reminded of the top five regrets of the dying. Among the men who climbed up with me that night, we reminisced on how we were to live our lives and for whom we would live our lives – it was certainly a night to remember.

The top five regrets of the dying echoed on that mountain and within each of our souls. I recently printed out these regrets and posted them on my wall as a reminder…

Graveyards are full of people who never realized their hopes and dreams.

I want to go over each of these regrets and share how I try to avoid them.

#5. I wish that I had let myself be happier

On our deathbed, we will inevitably come to question whether or not all the stress, anxiety, and struggle were worth it. For myself, I know and understand that there is a great treasure to be found in suffering. Suffering builds character, integrity, patience, kindness, humbleness, resilience, and most of all, an appreciation for all things. But, what about happiness? Was all the pain and suffering worth the fleeting moments of happiness? I say that it depends. It depends on how we define happiness.

If we define happiness as a feeling, then certainly the pain and suffering we experience in life is not worth it at all. Feelings come and go and often get us into trouble. However, if we define happiness as spending time on what matters most in life, then the pursuit of happiness becomes more meaningful.

Let’s say we define happiness as the pursuit of what we define as meaningful. If we rely on someone else’s definition of happiness, we deceive ourselves and only realize it as such when we come to the end of our lives. Instead, when we define happiness and pursue it, we should not have this regret.

I often find myself these days struggling between my beliefs and what I truly know what God has created me for. For example, at this moment, I find myself with a belief set mix of Christianity, Libertarianism, and Stoicism, in this order. Lot’s of -isms flowing around these days, so I try to avoid boxing myself into any of them at one time. Morally, I align with Christianity, but ethically I align with libertarianism. Stoicism creeps in from time to time to remind me that the change I want to see in the world starts with me. I find it’s a peaceful, yet powerful combination of frameworks for living. However, it is not without it’s challenges, and I struggle with them daily, especially these days. It is within the pursuit of this belief set, and the struggles they provide, that I firmly believe is my way to happiness.

#4. I wish that I had stayed in touch with my friends

Friends come and go, but sometimes there are ones that last forever. Right now I am very content with the friends that I have made over the years and continue to meet with the ones closest to me regularly. However, there always comes a time when life gets in the way and people move or move on, which should be expected. As we age, friends seem to get less and less and life gets more and more busy, not only for us but for those around us as well, again, this is not a bad thing.

I do wonder what will happen to the friendships I have made. I’m quite content being by myself and have proven that numerous times in my life. But, I do recognize that I must overcome the comfort of being alone to avoid this regret. There are times when I do miss living with friends and sharing stories and our lives over a meal. People are what matter most in life, and we must be vigilant in recognizing this truth and stepping out in faith to protect it. Time flies and we must be careful of this fact.

#3. I wish I had the courage to express my feelings

Now this one is tough for me. I’ve never been good at expressing my feelings, only articulating them. I do wish that I had the courage to tell some people I’ve met my feelings, and I do hope that I do so before I croak. I do make it a point to tell people that I do feel immensly. However, if you have been hurt as much as I have, you know that you think twice before sharing your thoughts and feelings with someone. Unfortunately, I usually come across as unfeeling, and I think that’s where the Stoicism plays its role. When I do share my feelings, it’s usually met with nothing. I understand people have a hard time empathizing with others, but come on people, at least try… I certainly do. I recommend everyone reading this read a book called “I Hear You” by Michael S. Sorensen – it will help you…

#2. I wish I hadn’t worked so hard

I find that work can be separated into to camps: your job and your accomplishments. Your job is there for you to work in order to provide for the life you want to live. You do not find you ultimate purpose in your job, that is what after work hours is for. Put your time in, stick to your work hours, and let your off time actually be your off time. As for achievements however, this is a slightly different story.

All men should be achieving something in life. If you are not, you are doing yourself a disservice. You will come to the end of your life and realize that you did nothing of importance. You will become another person in the graveyard of unfulfilled hopes and dreams. By the time you realize, it’s too late.

I’ll always remember what my Grade 12 English teacher said to my friend and I upon graduation. We talked about his retirement and told us that we were the last class he would teach. Reflecting on his career, he recognized that he really didn’t have anything tangible to show for it. He didn’t build a house, fix cars, start a business, or write a book. The only legacy he leaves is the students he taught, and who knows how many paid attention to his lessons or the impact he had on them. He’s a great guy, and I certainly wish him well. However, it’s a cautionary tale about the legacy you leave behind.

#1. I wish I had the courage to live a life true to myself, not the life others expected of me

Why are others’ expectations of us so powerful? So powerful in fact that they can change the entire trajectory of our lives. It’s cool to be liked, appreciated, and welcomed, but is it all worth the effort?

I’ve never really struggled with this one as I recognized from an early age that I was cut from a different cloth. Besides, I never fit in anyway, so I am quite content just doing my own thing. I laugh at those that don’t understand the fleeting moments we have in our lives. We should be focused on what matters most to us, as the rest is not worth the effort. Politics, religion, debates, and small talk mostly disgust me as talking about such things I deem a waste of time. Nothing productive comes out of discussing these topics in depth, so I just nod to get along really – as unfortunate as that sounds.

I think this is where my libertarian bent comes in where I do whatever I want to do, and you should do the same. If I get the results that you want, figure out what I am doing and repeat it. This of course works the other way as well. Whenever I’m asked to provide advice on situations, it usually comes down to this statement. The only other advice I give is that sometimes you need to retreat for a time to move forward. This works for me, so why would I not recommend this approach to others?

So, I pursue whatever I want. I pursue Christianity as I believe it’s the best way to live and understand life. I pursue libertarianism as I believe independent thinkers should be given as many options as possible in this life. Doing so can improve not only those of the bent, but also those who are too ignorant to help themselves. I pursue Stoicism as I know that real change starts with thyself. Improving myself improves the world. However, I also pursue other things such as music, reading, writing, programming, travel, hiking, biking, swimming, praying, meditating, yoga, video games, hard pursuits, unique challenges, once-in-a-lifetime opportunities, and everything in between.

I have the confidence in who I am to pursue anything my heart desires. Of course, most of these pursuits align with the trifecta of beliefs I’ve discussed, but sometimes I also pursue things that seem counter to them. And so this is where I find the most struggle. I truly believe that Jesus is the way, the truth, and the life and that by following Him I can fulfill what God has for me in this life. However, there are opportunities presented to me that I don’t believe align with tradition, such as writing a book, developing niche websites, and starting a business. Yes, I give all the glory to God, but I do have to wonder why God has allowed me to live outside the boxes most people put themselves in. But, if I were to die today, this would certainly not be one of the regrets I would have, not yet anyway…

Conclusion

I currently seem to be at a crossroads. On the one hand, I really have no regrets. On the other hand, I have recently been presented with opportunities that would break this streak, quietly tempting me.

So, I do what I do best, tell you what I am doing, and do it. I recently wrote a book, came to the end of myself during a three-day hiking challenge, and became a senior resource for a large company. Lots of changes, and I think I’m going through what’s called a quantum leap growth period – I’m excited!

We will see what happens, but for now, I’m doing my best…and you should too.