I used to believe that living with regrets was a terrible thing. Just thinking of the word “regret” used to leave a bitter taste in my mouth. It seemed like a negative. Grasping and holding onto memories was anathema to how I chose to live my life.

Stay in the present. Keep moving forward.

As I’ve grown older and wiser (though not yet wise!), I’ve developed a different relationship with regret.

Who says regret has to be negative? What if regret was all about understanding and learning from our past, for the sake of living a better life today? What if being clear about the things you regret not doing can help you gain certainty over your personal path to happiness?

I now embrace regret. I often think about things I’ve done (or haven’t done) that make me say “I should have done things differently!”

I don’t have many, but there are handfuls that I’ve reflected on as the years’ pass.

I’m now working my way, slowly but surely, towards the age of 40. A lot has happened in the past few years. New career. Marriage. Changing cities. New home. New interests. New friends. My daily routine is almost unrecognizable compared to how I lived even five years ago.

Now, as I reflect back, I notice that there are a few regrets I hold, particularly about things I did not do enough of in my 20’s. As I mention these things, it’s not that I ignored them as I was growing up. I did many of them throughout my teens and twenties. I just didn’t focus on them with a full level of commitment.

As Mark Twain said:

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

Here are the things that I regret not doing in my twenties. I’m listing them in priority order. The first item is what I regret the most. The last is the one I regret less!

1) Connecting with family

I’m now at the age where my parents are getting older. I’ve seen several members of my extended family pass away. With each passing year, I realize just how important it is to build memories with those closest to me. It’s challenging since my family lives throughout the USA and India. During my 20’s I didn’t think like this. I always thought there would be plenty of time to spend with my family when my career slowed down. We never know how long people are going to live. Cherish those who are around while you can.

2) Establishing a wider circle of close friends

I’ve tended to be someone who prefers to have a few friends that I am close too as opposed to many friends with varying degrees of closeness. I’ve rationalized this as being OK. Now, I realize that I could have built many more lasting friendships with a minuscule amount of effort. Making it a priority to reach out to others. Attending weddings and events without coming up with a reason why my not attending was OK. Listening to and being curious about others instead of trying to share my thoughts and opinions. Going out of my way to meet for dinners and drinks.

I do think that some friends naturally fall in and out of life as situations change. I also believe that with just a little care and effort, a circle of friends can both broaden and deepen. I’ve had dozens of great people enter and leave my life due to lack of care and attention. It didn’t need to be this way.

3) Living even more simply

It’s your money or your life.

For most of my twenties, I lived like a monk, and well below my means. As I moved closer to 30, and my income increased, I started to upgrade my wardrobe, housing situation, and my car. Beyond the big ticket items I purchased, I also just acquired a variety of things that seemed crucial at the time. Electronics. Accessories. Furniture. Books. Many of these items have since been given away or are still taking up space in a storage unit we are renting at the moment.

Living simple is a mindset, and more important than the monetary savings, it creates an inner sense of freedom. When life isn’t encumbered by things, you can connect with what really matters. Yes, there is a life-changing magic to tidying up.

4) Building healthier routines and habits

Waking up earlier (like 5 am early). Consuming minimal caffeine and alcohol. Writing. Meditating. Eating well. Yoga. There is a whole slew of habits and routines that would have served me well in my 20’s. These habits, like waking up early, for example, have a remarkable and compounding effect on productivity.

All the practices I mention are things I currently do and have done in my 20’s. Yet, there would often be months (or in some cases, years) where I would lose focus on these routines and adopt more unhealthy patterns. I’m now seeing how sticking to these healthy ways of being is the key to personal satisfaction and happiness.

5) Getting out of my comfort zone

There are a lot of things I did in my twenties that got me out of my comfort zone. Big work projects and presentations that demanding insane levels of responsibility and confidence. Ironman Triathlons. Travel to foreign countries alone. Stepping up to go from yoga student to yoga teacher.

But, in hindsight, I realize that I had a lot of room for more activities that would have pushed me out of my comfort zone. Whereas I might have done a few things a year that really stretched me, I could have done them each month. Profound growth would have emerged. In particular, I would have gone out of my way to advance my career and personal life by taking more risks to meet and build relationships with new people.

6) Investing more in person development

In a previous post, I mentioned that I’ve probably spent over $40,000 USD in the past 16 years on personal development. Goal setting workshops. Speed reading courses. Tony Robbins Mastery University. Too many yoga workshops and retreats to count. Online courses and programs in all areas of personal development. The amount of work I’ve done on my inner being is higher than what I observe most people doing. This was on top a bunch of training my employer paid for.

Yet, I do wish I was more intentional at spending time working on the right skills and training based on what I needed. Instead, I would just attend things that interested me. I also should have invested even more with coaches one-on-one. I’ve found that direct coaching produces the best results. Hiring a great coach isn’t cheap, but the payoff is immense (5–7X an initial investment based on several research studies).

Successful companies set “Research and Development” budgets to ensure they continue to innovate. I believe that people should set a personal development budget each year to ensure that they are continuing to grow. In hindsight, I would have invested more to sharpen skills around writing, influence, negotiation, learning a foreign language, voice/speech coaching and more. Most importantly, I would have worked with a coach to identify blind-spots and move through them.

7) Building my personal brand

I spent my entire adult life working for a great company, Microsoft. I also taught yoga for many years, which expanded my circle of friends and made people see me as more than the “Microsoft guy.” Now that I’m no longer working for a corporation, I’m noticing how much I ignored building a personal brand that would support me over the long term. Inside Microsoft, people knew who I was. Outside of the company, people have no clue what I’ve done.

I think this applies to many corporate workers. They can do outstanding work inside their bubble, but once they leave (or are laid off, down-sized, etc.) they struggle to rebuild the trust with other potential customers and partners. I wish I spent much more time building my personal brand – as a product manager, planner, strategist, and technologist. I could have done this through blogging, speaking or through networking with a broader group of people.

8) Starting my side business

In 2008 I started my business, while I was working at Microsoft. My business was a sole proprietorship (should have been an LLC, but I didn’t know what I was doing). My service was yoga. Creating my business allowed me to write-off any and all expenses relating to my practice. I never had any income goals for teaching yoga. It was (and still is) and passion and while I earned a few bucks for teaching each class, the pay was nothing compared to my corporate job.

This was all good. Yet, I wish I created a business that had significant income generating potential. Doing so helps to offset taxes. It also provides the potential for a smoother exit from corporate life when the time comes. Running a business can be fun. It’s a great way to serve others. It’s also remarkably challenging, as I am now learning.

9) Traveling more

I think I’ve traveled to about 25 countries (one day I’ll count!). Every few years during my twenties, I went on adventures to places like India, China, Peru, Ecuador, and more. I don’t regret doing more international travel. What I regret is not taking advantage of exploring my backyard.

Over the past few years, my wife and I have developed a habit of exploring the areas around where we live. Now that we have moved to Colorado, we want to get to know our new home. Every few weeks we are checking out a new mountain town and seeing what restaurants the Denver area has to offer. I remember how much a creature of habit I was in my 20’s. I would eat at the same places, hike at the same trails and get into my regular routines. While I was active, I wasn’t exploring my backyard. I missed out on a lot of new experiences by not broadening my horizons.

Conclusion

Some people might disagree with this post. They might say that everything happens for a reason. Regrets aren’t healthy. I do not agree. I’m not holding onto anything by stating my truth. It’s only through examining our personal stories that we can set forth to live a more fulfilling life in the present and future.

These regrets are real for me. They also help me understand and set my current priorities in life. It’s no surprise that my current lifestyle takes care of the things I either ignored or didn’t focus on when I was younger.

Hindsight is a powerful tool. We can all use it to learn from our journey and shape a path for our future that will be more fulfilling.

I’d love to hear from those who read this post. What is one thing you regret not doing in your past? How will this shape your life starting today and moving forward?