There are a few markers each year that have the tendency to knock you back into a state of reflection. Times that can finally push you to drop off of the ever-moving treadmill of life, exhale and look at the water you’re standing in and the reflection that it shows.

Naturally, one of those moments is a birthday. A day where you can acknowledge you’re now a year older and (hopefully) a year wiser. People ask at certain milestones, do you feel different? The truth is that on the day you turn a certain age, nothing actually happens out of the ordinary. In fact, most days aren’t out of the ordinary. If they were, then they wouldn’t be “ordinary”.

But I’m not the same person I was a year ago, and neither are you. That’s not because of the day we were born, but rather the collection of days that occur between each revolution around the sun.

For me, this was a year of dedication. Dedication to my craft of sales, which led to a promotion and responsibility of leading a team. Dedication to my “side hustle” of podcast and blog creation led to conversations with some of the most inspiring people on planet Earth, modest notoriety and lessons I won’t soon forget. Dedication to the constant pursuit of learning, devouring as many books, podcasts and thoughtful articles that I could get my hands on.

It was a year of adventure. I traveled to three foreign countries, nearly a dozen states and some of the most breathtaking places I could have imagined. I ran on the beaches of Thailand, went dogsledding in Park City and had the best lunch of my life on an unkempt stoop in Florence. The adventure led me to sign up for the most challenging physical endeavor of my life, a Spartan “Beast” race totaling 15 miles and 30+ obstacles traversing Squaw Valley in Lake Tahoe, CA.

Most importantly, it’s been a year of prioritization. It’s the most I’ve seen and spoken with my family since graduating from college 4+ years ago, despite living thousands of miles away. I’ve become closer to my parents, sister, and grandparents than I can remember. I’ve fallen into the deepest love of my life with my girlfriend. I saw one of my best friends get married and have formed new friendships with people who were complete strangers a year ago.

I’ve felt inspired and (hopefully) inspired others in return.

But, despite what the founders of Instagram want you to believe, life is not a highlight reel.

My dedication to the crafts I love has caused me to fail more than I ever have. My new job has driven my feeling of imposter syndrome just about every day of 2019. I’ve felt burned out and questioned where my future was heading.

Despite my highlight reel of adventure, I am still quite afraid, still quite anxious. Afraid of trying something new. Anxious of other peoples’ opinions and about the days and years that lie ahead. I dread the amounts of likes, comments, claps and every other miscellaneous reaction that one can give to this article I’m writing.

Despite the prioritization and love I feel from my “core people”, I sometimes feel out of place. In one of the busiest cities in the country, I’ve felt lonely. The highs of love have equally brought lows of stress, jealousy, and fear of vulnerability.

In reflection and in progression, there are two ways to approach these moments.

The first is to look at the aggregate. How am I doing vs. me a year ago? I feel wiser, healthier, more energized, more loved, more thoughtful and happier than last year. Moving forward, I have big, scary goals staring at me. I’m highly optimistic at the macro-life I have ahead of me.

Annie Dillard once noted that “how we spend our days is, of course, how we spend our lives”. The second approach, therefore, would be to break this reflection into my daily life. Looking backward, each day was far from perfect. I often felt tired, aggravated, self-conscious, anxious or distressed at some point in the day. But every day, without fail, I worked to get 1% better. I tried to love & prioritize those that are important, I pushed towards my goals, I worked to get healthier, wiser and more fulfilled. Moving forward I will continue to do the same.

“How we spend our days is, of course, how we spend our lives”

And I think that’s the thing I’ve learned from staring in the mirror of the past 365 days with a vulnerable, truthful eye. To focus on that daily improvement, daily happiness and the simple pleasures that can bring a successful day.

John Wooden once said that he aspired to “make each day his living masterpiece.” Imagine that? Following Dillard’s logic, this would create a masterful life. So, regardless of when your birthday is and how your year has been so far, let’s work on that as our goal. To make each day, and therefore our lives, a living masterpiece.


  • Tom Alaimo is a obsessed with helping others reach their full potential. He works in B2B sales and runs Millennial Momentum, a blog & podcast focused on millennial personal devleopment. When not writing or podcasting, you can find Tom playing tennis, running endurance races or reading a good book in San Francisco. For more info, check out