A Letter to My Future Self: Will I Be Happy?

Many of us get trapped by the day-to-day monotony of our lives. We’re not happy, but we’re not miserable either, and in this state, we are often unwilling to change. But if we are reluctant to create a new path, our future is guaranteed to remain the same.

So here’s the question: If nothing changed, and you met your future self ten years from now, would you be happy?

What would life be like for you? Would you be stuck in the same ruts? Would you complain about the same problems or feel cornered by the same mental blocks and broken mindsets?

If so, you are not alone. 

Are You Changing or Staying the Same?

Imagine going to a party. Maybe it’s a backyard bbq, a 40th birthday celebration, or the latest art exhibit in the trendiest part of town. While you’re there, you run into an old friend. You haven’t seen this person in over ten years, and you’re excited to catch up and see what’s new. 

Unfortunately, your excitement is short-lived, because rather than hearing about the highlights of the last ten years, you receive an earful of complaints from them.

It begins with negative comments about your friend’s career, then traverses a winding list of grievances about money and relationships. Your friend is unhappy and looking to vent, and you are more than willing to lend an ear.

You listen intently, all the while realizing you’ve heard these stories before. Ten years ago, your friend was telling you similar tales. Back then, she was disappointed and disgruntled about the very same things. It seems little has changed since you last saw her.

Now turn the tables on your conversation. This time, imagine you are talking as your friend listens. Is your life different from the last time you spoke? Are you still unhappy about the same things?

Questions to Ask Yourself

Fast-forward ten years into the future. You arrive at this same party a decade from now. What is your future self doing? Do you like the vision you see?

What if everything in your life remained the same for the next ten, twenty, or thirty years? Would you be happy, content, or downright miserable?

A Teenage Letter to My Future Self

When I was a teenager, my favorite English teacher asked us to write a letter to our future selves. Unfortunately, I have no idea where I put it. If I could find that letter from my childhood, I’m sure it would talk about money, jobs, love, and friends who seemed like they’d never part ways.

As I wrote that letter, I envisioned myself through the eyes of a teenager. I wrote about the things I cared about in my youth, but I failed to see that my priorities would change.

A letter to my future self would focus on the problems of this moment. But, what I need is a pretend letter from my future self that I can read right now.

So what would I like my future self to say?

A Letter to My Future Self

Dear J,

First, you should know that your greatest accomplishments will be moments you never could’ve imagined. For all the things you thought might happen, your life is better than every unique path you could’ve predicted.

The most memorable events arrived when life didn’t happen the way you expected. The most significant discoveries all came from unforeseeable opportunities, so keep your eyes open and explore new possibilities. Never get too comfortable or complacent, and keep searching for new avenues for inspiration.

Don’t follow the guidelines and expectations set by other people. Ignore the naysayers before you begin to believe their distorted points of view. Instead, surround yourself with cheerleaders. Listen closely and you will find them.

Fear can prevent you from moving forward. It can keep you locked in your current mindset and force you to believe that you are not worthy of an amazing life, but fear is not all bad. Use the fear of death to help you act bravely. You get one chance at this life, so don’t waste your time running in never-ending circles.

Cast aside your beliefs about success, money, and accolades. Climbing the corporate ladder will not make you happy, so don’t feel guilty if you don’t want a career anymore.

Please, do not be afraid to fail. You might not believe me, but your biggest mistakes will lead to your most memorable triumphs.

Remember, when you toss your rock into the pond, a tsunami won’t come crashing back to shore. Few of us make enormous impacts with just one stone, so instead, wait patiently for a tiny ripple. Then toss in some more.

Lastly, if you don’t like the path you are on, you have the power to alter it. Please don’t change everything all at once. Instead, start with tiny steps and take your time. Take small risks and search for new adventures.

When you feel stuck, think about your future self. Picture yourself ten, twenty, or thirty years from now. Then, imagine chatting with the person you want to become.

All the best,


Making a Change

Do you feel fulfilled right now? If you don’t, what’s missing? Think about the key components that make up your happiness. They may include your relationships, career, health, family, skills, knowledge, and your sense of community.

Which of these make you feel content and which need to change? If you could improve just one thing, what would it be? 

Now, start there. The goal is not to adjust everything in your life all at once. Instead, it is to figure out what you want to keep and what you want to do differently. 

Life is about choices. So what are you choosing? Are you choosing to remain the same or to live life differently?

6 thoughts on “A Letter to My Future Self: Will I Be Happy?”

  1. Oh, my I just had a trip down memory lane. I just read a few of my letters to myself 9, 17, and 18 years ago. So much has changed, even in my wildest dreams I couldn’t picture where I am today – for all the right reasons.

    It is hard for me to image life being better than it currently is but there are some adjustments that I can make. Mostly making space for self improvement.

    I wouldn’t have explored those memories without your post, thank you!

    • I’m jealous that you still have your old letters. What is your biggest takeaway in reading them? I too am making space for self improvement. It is an ongoing process that I never want to end!

      • Well, my letters are a bit all over the place. The first round (2003), is a deluge of what I was doing but with little insight (no car, no boyfriend, miss home) but of the few things I listed that I wanted to do I accomplished (enlisted for only 4 years, went to college, lived in the Dakotas). The most recent letter (2012), has more details of what I was doing and only mentions one regret. But, I turned that regret around when I did finally travel to Europe.

        My take away is that I spent 99% of my time dwelling on what was going on and not much about what I wanted for the future. It has only been recently that I have been writing down specific things I want to accomplish and trying to move towards those goals. ‍♀️

        • I love this! I also tend to dwell on things, but as I grow older I try to look happily to the future. Finding the right balance between reflecting on the past, focusing on the present, and projecting to the future isn’t always easy, but I keep trying to get the balance right anyway.

  2. I’m happier than I used to be, but that’s not unusual- people seem to get happier with age. I’ve always wondered why. Could it be that older people are less concerned with what people think of them? I notice I care much less about that now. Or maybe the older you get the less you compare yourself to others. Something to think about.

    • Interesting. I don’t think being happier is the norm. At least not in my limited circles. I have many friends my age who are unhappy and wish life took them in a different direction. I myself am much happier for the reasons you mentioned!


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