Hi, it's me.
You don't know me, but in time you will. I have the benefit of time and experience on my side and wanted to share some thoughts with you if you're willing to listen. If you receive this, please know that it comes from a good place.
Let's talk about that time in high school when you ran with the cool kids for a short while before they rejected you. What they rejected was how hard you were trying to be something that you weren't. You'd think this experience would have taught you not to repeat this mistake, but you'll end up making similar mistakes. The good news is that you'll find your own path, make your lifelong friends, and care less about what others think of you. Please Don't be so hard on yourself because we live and learn. You'll get there, but I know if you could read this—you would have gotten there faster.
How about one of the best decisions you made in your youth? One evening you came home from work and told your mother that you knew what you wanted to do. You knew that you had a visual talent and felt compelled to see if it could take you somewhere. You didn't feel good enough for a prestigious design school like Pratt, but you got your mother to agree that if you got accepted, you'd work harder there than you ever did in high school, and this would be the foundation you will build your future on. Never second guess this decision, even when you're up all night working like mad to finish a project that you want your talented classmates to respect.
You're going to fall in love young—too young. You won't know any better because you will think "this is as good as it gets", but you were too young to understand how life truly works. On the bright side, this relationship will bear fruit in the form of two boys who you'll love unconditionally and will give you tremendous purpose in life. They will allow you to offer the fatherly guidance you didn't have, and they'll challenge and reward you in ways that force you to grow and mature from a young man into a fully functional adult. And you'll find love again and have the experience and wisdom to know what this word should really mean, as complex and mysterious as it is.
You're going to take a leap of faith and leave your hometown of NY, where you started your career to land in the midwestern city of Chicago. You'll lose your Long Island accent and get homesick, but you'll grow an appreciation for the more modest and hard-working style of midwesterners. At first, Chicago won't know what to make of your New York ways, but you'll adapt and change your professional and personal style. This adaptation will serve you well in the years to come.
As the early days of social media literally change the Web, you will transition from a designer and "creative" to a strategic thinker who knows how to execute. You are going to find yourself in the weird and wonderful position of developing a professional "following," and the attention will make you feel uncomfortable. Don't be. Go with it because it won't last forever, and while you don't know it, you'll actually be positively impacting people's lives as you help yourself.
You'll stay working on the "agency side" for too long. You'll take a risk to do something different, and it won't work out—so you'll go back to what feels familiar. However, you will still grow professionally and work with some absolutely top-notch people and clients and you'll learn much in the process as the internet re-shapes the world in some ways you predicted, and in other ways, you didn't.
You'll experience much in your adult life: from the joys of bringing new lives into the world to the emotional toll that comes with divorce to the appreciation of seeing your parents grow old to the historic moment when the country that your parents immigrated to finds itself grappling with a global pandemic and civil unrest at once. In some ways, the culmination of these experiences, both good and bad will help you stay grounded when the world feels unmoored. You'll be grateful that you've built so many meaningful relationships, so don't ever feel like you aren't "productive" when you're investing in someone else and forging a new connection.
As previously stated, you'll make mistakes—some you'll learn from and others less so. Only invest in a business model you understand, only invest in others that respect your time, and only be as hard on yourself as much as it makes you better vs. worse.
Don't forget where you came from, what you believe in, know who you are, and find ways to serve others. Time will go fast, so make it count because we only have so much time here.
With love and respect
Older (and wiser) you