Sell Yourself the Best Year of Your Life

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

This quote, by H. Jackson Brown (but often attributed to Mark Twain), has always resonated with me. I loved it so much that it was the quote I chose to accompany my picture on the leadership page of my old company’s website. As I sit here, unemployed, in our 27 foot Airstream home on wheels (AStreamComeTrue) somewhere in South Dakota, I can’t help but chuckle a little at that. A little over three months ago, I walked away from the safe harbor of suburban life and a successful career to explore, dream, and discover. I decided to sell myself the best year of my life.

So, how did I get here? My wife and I had been toying with this idea for a long time. We started dreaming about taking an extended period of time off from the hustle and bustle of “normal” life to travel about 15 years ago. Those 15 years have flown by and time seems to only be accelerating. My dad passed away from cancer 12 years ago, a week before my son was born. I can vividly remember walking in the door of his house from the hospital after he died to see a bouquet of balloons rising out of a coffee mug that read, “Happy Retirement!”. That was a big wake up call at the time and I have thought of that moment often over the past 12 years. If you want something out of life, what the hell are you waiting for?

Neil Young sang one of the best quotes in Rock ‘n Roll, “It’s better to burn out than to fade away.” This is another quote that has always really stuck with me. Often, when people leave jobs, they say it is because of burn out. The funny thing is that burning out is a positive thing. You get burned out because you go all out, all the time, because you love it. I had reached a point in my career where I was no longer burning out, I was fading away. No longer did I love what I spent most of my waking hours each day doing. I, hopefully, had a lot of life left in me so I needed to re-energize. I needed a change.

Sell Yourself the Best Hour of the Day

Charlie Munger, Warren Buffet’s right hand man, started his career as an attorney. For most attorneys, the billable hour is seen as the holy grail, the key to success. Many other professionals think like this as well. That’s unfortunate because they are missing the long view and the big picture. Charlie Munger knew this, so he made it a habit to “sell” himself the best hour of the day by “sacrificing” a billable hour each day to invest in himself. He would work to learn and increase his knowledge or work on side projects during this hour each day. I think it is safe to say this ended up working out well for him.

I decided to take this concept a step further and sell myself the best year of my life. As I meet more and more people during my travels, I am beginning to realize that I am not unique in this line of thinking. There is plenty of research out there that indicates the positive benefits of sabbaticals – increased happiness and well-being, decreased stress levels, and greater levels of engagement. Unfortunately, not  many people outside of academia have the ability to take a sabbatical. Some can work with their employers to lake a leave of absence; but, let’s face it, that’s not how real life works most of the time. That’s why I think that more people should try to reap the benefits of a sabbatical in alternative way – by selling themselves the best year of their lives.

Your Best Year

We all have different ideas of what the best year of our lives would look like. Your best year could look something like the following. It could be something totally different. 

• Try to start that business you have always dreamed of
• Try out another job or career you always dreamed of
• Do volunteer work in a third world country
• Take an extended period of time to improve your physical and mental health
• Recharge your batteries to keep from fading away
• Write that novel you have always dreamed of
• Record that album you have always dreamed of
• Develop new ideas and innovations for business
• Achieve a specific goal – hike the Appalachian Trail or sail around the world
• Spend time with your family traveling around this beautiful country to hopefully instill a sense of adventure in your children all while figuring out what you want to do with the second half (hopefully) of your life

Remember that this is a year, so it should be something worthy of a year. Think big and bold. Don’t pass judgment on your idea too quickly or say, “This is just not possible.” Define your best year first and then worry about (and figure out) how to make it happen.

Sell Yourself the Year

When you decide to do something big and bold, you must recognize that it will cost you something. If it costs you nothing, then you have not gone big enough. Not everyone will need to quit their jobs or sell everything they own to achieve their goal but some will. When you sell yourself the best year of your life, you could end up paying for it in one or several of the following ways.

• Money. Most of these years will cost money in one fashion or another. I can think of nothing better to spend money on than dreams though.
• Time. All of these years will require an investment in time. You will spend your time planning, you will spend your time preparing, you will spend your time doing, and you will spend your time reentering your previous life. You will spend a year out of your life but can you think of a better use of that time?
• Energy. This shouldn’t be easy. You may have second thoughts along the way but this happens with every good adventure in life. If you don’t feel completely exhausted or don’t question your decision at least once during your year, you may not have gone bold enough.
• Your job. You may need to give up your job to pursue the best year of your life. Recognize that, if you do, this will likely require other sacrifices as well.
• Career. Taking a year off mid-career may slow down your advancement through that career path. It may take you a little longer to climb that ladder if you jump back in. Future employers may frown upon “time off” from your career. If that worries you, think if that is the type of person you would want to work for anyway.
• Relationships. Some of these years may require separation from your family, friends, and community. Don’t worry though. If these relationships are strong, they should still be there when you are done. They should still be there when you are gone.
• “Respect”. Not everyone will like your idea. Some people will say you are crazy, you are irresponsible, that you are thinking of yourself. So what?
• Comfort. You should be moving way out of your comfort zone during this year. If you are going big and bold and paying for it in one of the ways listed above, you should feel uncomfortable. Embrace that feeling.

Get Going

Nike’s old slogan of “just do it” makes for great marketing and for great pep talks. But, if you are doing something big and bold like selling yourself the best year of your life, it is going to be a bit more involved. Some of the ideas below may be common sense, but this is how we slowly dove into the best year of our lives. This may look a little different depending on what your year looks like, but the following four steps should still apply.

• Take time to clearly define what the best year of your life may look like. Remember, this is going to be far from free, so make sure you know what you are buying first.
• Once you know what your best year will be, tell those closest to you that you are going to do it. There is no better way to hold yourself accountable to actually making it happen.
• Break down what you need to do into manageable steps so that you can have small wins along the way. For us, this involved small steps like developing a budget, putting a plan in place to save enough money for a year off, decluttering and selling the excess things in our lives, researching the ins and outs of being traveling vagabonds (insurance, domicile laws, taxes, etc.), buying the Airstream we would spend a year on, etc.
• When you approach the point of no return, cross it. “Burn the boats” as the Romans used to do when going into battle so that there was no retreat and victory was the only option. For us, burning the boats meant selling our house. Without a house, we had nowhere to retreat to.

I hope, if nothing else, this gets you thinking about what the best year of your life could look like. Life can be extremely difficult at times, so you may not be in a position to sell yourself this year at this time. But, life has a funny way of working out and, one day, you will.

If you think something is holding you back from realizing a dream, think really hard about if it is really holding you back or if you are using it as an excuse. We live in a time where most of you reading this are of a socioeconomic status where this is totally possible. Most of your basic needs are likely covered. You don’t need as much material wealth as you think and investing a year in yourself will not kill you. In fact, it will probably make you better. Life is short, get out there and live it.