I’ve always been averse to making big changes and taking chances when it comes to my career. Much of this has to do with being the provider and a fear of failing to keep my family well-off.

As you grow older you realize just how precious life is and having turned 39 in July, I realize windows are closing if I want to hit a lot of my bucket list items while I am still in my best years.

Even though I am likely in the best physical shape of my life and have an amazing family I still constantly get down thinking about all the things I have not done. It is a bit selfish, knowing I have done more than many get to do in an entire lifetime, but I have never been one to be satisfied with what I have.

I sit here now, knowing I could easily take ten years off without any source of income and live well but also wonder if the uncertainty would drive me crazy. I spent my thirties building a business, and a family, that has set me up very well for whatever number of years I have remaining. One major hesitancy of walking away is that the business is thriving, and I continue to love what I do with so many ideas and plans to continue building it, but at what cost?

Time is the most valuable commodity in the World and running this business is sucking up a lot of it. I am putting in seventy-hour weeks with my weekly routine generally being up at 4:30am and working until 3pm with about an hour of breaks, then playing with the kids 2 to 3 hours, having dinner and back at the desk for an hour of nighttime work before maybe being lucky to spend thirty minutes reading a book before getting to bed and hopefully getting six hours of sleep. I have full Saturdays with zero work and usually at least ten hours free on Sundays, at least.

As much as I love my career, I also hate the parts that keep me sitting at a desk so often, which is not healthy, and the inability to have one of those schedules where I can get away without worrying, even more an hour mid-week. Things are only going to become tougher with the kids entering their school years and all the activities that will consume more of our time, I have no idea how people do it with more than two kids. I hate that I have to set aside a 2-3 hour block on a Friday to get my one mountain bike ride per week in and knowing I will have to come back and catch up with two hours of work, and that I can not just up and take a ride when I want during the week.

Another Summer is coming to a close where I did virtually no fishing and played zero rounds of golf, two of the things I enjoy most. That is not living, that is just grinding with no end in sight. I scroll through my Amazon “Books to Read” Wishlist and start calculating at the current rate how long I would need to live to get through them all, I know…stupid shit like that gets me anxious. I spent a lot of the Summer running and biking, two things with defined times but would love to just be able to backpack into the mountains without having any scheduled time to return. I have always had too many hobbies which makes it difficult to allocate time to each accordingly and then there is a long list of new skills and hobbies I want to learn.

I know if I were to walk away that the business would be tough to just restart years later, and I would likely need a career change if I want to go back to work. I’ve always wanted to do something more meaningful to society or something that intersects with passions like nature or sports but also know I have a very rare and valuable skill for investing and it is always hard to walk away when you are still in your prime, athletes know this all too well.

I have said for years I want to pivot into something that can allow for a better work/life balance but have not taken enough action. I am putting a lot of time, and money, into this new OptionsHawk Dashboard App that could open some major opportunities, and that excites me. I likely should sell an ownership stake in the company to a firm that could instill a team of people to grow it to what I know it could become. Based on our strong growth, high profitability margins and strong brand OptionsHawk is likely worth more than a lot of these unprofitable software companies with $50M+ valuations. At this point I am not even sure what I am working towards any more other than building an even larger nest egg that I will never enjoy, but money is like an addictive drug and the more you make the more you want to make and this even as I am not someone that cares about buying expensive things or living lavishly. The best things in life truly are free if you think about it, learning, relationships with others and the outdoors. I always made fun of these billionaires that are still working past the age of fifty and here I am setting myself up to be that same idiot, though not quite a billionaire.

I really need to take action over the next year to set me up for some major life changes and hope I have the guts to follow-through and take some major risks. I also need to do it for my health. Although on nearly every account I am as healthy as an ox, I do continue to have persistent high blood pressure readings which is partly due to genetics/personality and partly to work-induced stress. We picked the perfect house and location with our move to Montana in April though it is really making me want to have more time to experience all there is to offer here in terms of outdoor adventures.

In terms if the things I would do with my time if I took a five-to-ten-year hiatus, the following come to mind:

• Family – Spending more times with my family is important and its tough allocating time as we grow older with so many things pulling us in different directions. Most importantly I want more time with my kids, we never get these pivotal years back, and there is so much I want to teach them and experience with them. My new Mountain West schedule has allowed me to get 2-3 hours of free time each day during the week with them, but I really want to be able to taking multi-day adventures, coach their sport teams and overall just be in the moment without the stresses of work weighing on my mentality. My kids are amazing and bring me so much joy and I want to feel what I feel when we are hanging out 10X before they move on to starting their own busy lives.
• Travel – Nothing is more enjoyable or as memorable as the trips taken through the years. I know some of this will be restricted by needing to have the kids in school for their education but even three-day-weekend type trips can be amazing experiences. In the US alone much of the West I want to explore in Colorado, Idaho, Utah, Arizona, Wyoming, Oregon, Alaska, Hawaii and New Mexico doing the things I enjoy like hiking, biking, fishing, golfing and visiting historic sites while eating/drinking well. In terms of overseas travels there are countless places I have yet to see like New Zealand, Iceland, Croatia, Scandinavia, Africa, Peru, Argentina, Africa and many more.
• Read & Write – As previously mentioned, there are so many amazing books I want to read, mostly about history and just finding long stretches of time to read sounds like an absolute dream, and this could tie into travel as well. I also have some ideas for books I want to write, both in history and children’s books. If I was looking to write for monetary gains I would obviously put together a book on investing/trading but that sounds boring to me. I always feel so good after reading a great book and continuously learning is a way to keep the brain young. I watch very little TV these days, its such a waste of entertainment hours.
• Meet New People – Building relationships with people is very hard when you have very little free time and I feel like traveling is a time I get to talk to new people and have really interesting and memorable conversations which I love. Who knows, maybe a conversation/meeting could set me up for my next act. I always tell my wife I am not a people-person yet any time I am put in a situation with people I tend to have some incredible conversations and I secretly do enjoy those times.

Walking away from what you know and into the unknown takes a truly special person and I hope I have it in me to make that move one day. Knowing what I know about myself, I feel like I will just keep on moving those goalposts until it is too late, and that weighs on my subconscious very single day. I had told myself saving $5M would be enough to retire and now I changed it to $15M after a few adjustments. I really just need someone to force my hand although I know it would be really difficult for me to not be involved in markets in some capacity.

Being incredibly driven and unable to settle for anything but the best has been both a blessing and a curse in this life. But, unlike Tom Brady, I want to go out on top.