Yesterday, while biking the Katy Trail in Missouri, we met a retired couple who were biking across the state. This is kind of common for us. There are really only two types of cyclists we meet: retired people and wealthy mid-30’s types who are spending their annual vacation sprinting across the country before returning to their job. There are a few exceptions, we did meet a guy who is our age and also bicycling every state in the US. And we met a woman in her 20’s who is currently biking across Europe and working on farms as she goes, but they are the exception.
Anyway, back to the retired couple. They were pretty much the archetypes of the retired cyclist. They had always wanted to bicycle across the country (and maybe the world) but decided to put it off until retirement. Through the years their bodies started to weaken and they got overweight, but their bank accounts grew. They put off the dream of biking across the country because the timing wasn’t right. They wanted to make sure they had enough money to be secure, they didn’t want to leave their jobs of 30 years, they wanted to make sure they had the right equipment, etc. Now that they have all those things their bodies just aren’t up to the task, so they settle for a weeklong ride across Missouri before heading home. In addition, new issues that they couldn’t have predicted have sprung up, including an ailing mother who needs constant attention. Now, their time and money goes to taking care of her instead of their jobs, and their dreams are going to be filed under “fantasy” instead of “biography” forever.
There are many lessons that get pounded into our heads while we bike across the country, one of the most potent is The timing is never right. And that doesn’t just refer to adventures, it really applies to all dreams and important decisions. Whether you want to propose to your significant other or need to break up with them, you want to go back to college or start a new career, adopt a baby or get sterilized, sail the ocean or climb a mountain, take up yoga or cut soda out of your diet, rebuild a relationship with your parents or cut poisonous family out of your life, there is always going to be a reason to say no and stick with the status quo.
Take breaking up… every time I’ve broken up with someone I knew weeks, or months ahead of time that we were heading in that direction. I knew we weren’t compatible long term but we stayed together. I also wasn’t really enjoying the relationship in the present either, I stayed with them because it was easier to avoid what I knew what must be done. Instead of actually breaking up I put it off and put it off until things got really bad, unrepairable, with no friendship to salvage. If I had broken up with her when I knew I should of, but we still had a friendship, it is possible we would still be in each other’s lives.
I don’t think I’m alone in this. Isaac Morehouse discussed how it is never the perfect time to adopt recently on his podcast (a podcast you should all listen to because it is awesome). Margaret Atwood said “I have long since decided if you wait for the perfect time to write, you’ll never write. There is no time that isn’t flawed somehow.” If we wait for everything to be perfect we will never get anything done, we will day with dreams staying in our heads instead of becoming reality. I realize the risk of taking chances can be high, and dreaming is easy. TK Coleman brings a slightly different take on it in his blog, “The dream is private. The pursuit is public. This distinction alone explains why many people never get around to following their dreams”
Maybe my old age is making me less risk averse. As older generations of family members get sick, as my own parent’s approach retirement and their bodies aren’t healthy, I am becoming intimately aware that my own chances to live out my dreams are running out. Every time I fall asleep that is one more day that has passed where I didn’t try to invent something that has been in my head for years, didn’t start writing a book, didn’t start learning a foreign language, didn’t start an exercise routine to be my best, didn’t break a habit that is unhealthy and makes me feel guilty. And every time I don’t do something I dream of the excuse is the same basically the same, the timing isn’t right. It may take many forms like “I’m too tired” or “sitting on the side of a road in rural Missouri isn’t a good place to knock out a bunch of push-ups and planks” or “I don’t have anything of value to write” or “I don’t have the time to make it work right now”. I am sacrificing the good for the perfect and violating that rule of Gen George Patten “A good plan today is better than a perfect plan tomorrow”.
This is an area I need to improve on, it is an area I think many humans need to improve on. For whatever reason, maybe a product of evolution and maybe a product of our society (or both), we put off what we want until we can no longer have it. In some ways that is an easy way out. If you always wanted to climb the Pacific Crest Trail but the timing was never right until retirement you have an easy excuse, and when you retire your body can’t do it anymore which is another excuse about why your dream never came to completion. I think that is unfortunate though. I think the world needs more people completing their dreams and less people working 9-5 jobs for 40 years to put money in a bank account. I don’t think people regret chasing their dreams, even if it means giving up security. Quitting your job to become an entrepreneur, even if the venture fails, is better for the individual, the family, and our society than if a person stays in a secure job for a year.
This world needs more than just dreamers, we need dreamers who make those dreams public and pursue them. We need to realize that life, our circumstances, and the world will never be perfect, and we should push on anyway.
Wandering Oak 
Good timing on the post. It was a great read. Has me thinking what type work you do that allows you to live anywhere?
I do writing and research for a small community development consulting firm based in South Carolina. Our clients are mostly non-profits and local governments who need assistance with meeting federal requirements for environmental reviews and such. I didn’t have this job when I started my three-year bike ride though. I quit a decent job in Los Angeles and decided to just make things work, after a few months on the road this opportunity presented itself because of some of the connections I made in the past.
My partner also has an online job. She is a dietitian for an Australian company and helps do meal planning, answer forum questions, and updates their database. She was working for them in an office in LA and basically told them that she was going on a three-year bike ride and she would love to work for them remotely, if that didn’t work for them then she was going to quit. They took her up on the offer and it has been working great for over a year now. She basically did what Tim Ferriss describes in “4-Hour Work Week”, though neither of us had read that book at the time. I highly recommend that book if you are in a job that is primarily online and theoretically be done from any computer with an internet connection.