50 Reflections on Life & FIRE Upon Turning 50

As I write this, I’m just a few days away from turning the big 5-0 (Allison got there last year). I’m excited! Hitting the half century mark is one of the most profound milestones in a person’s life.

Of course all milestone birthdays feel important, like turning 20, 30, and 40 (and I assume 60, 70, etc). However, 50 is a big one. It’s the age of the proverbial midlife crisis. If you’re lucky enough to reach age 100, you’re halfway through your life now. 

When facing a major life event, it can be helpful to reflect on what you’ve learned so far. Here are some of the most important lessons I’ve learned over the past five decades. They’re in no particular order, but I’ve divided them into different life categories to make them easier to digest.

 

Health


Without a foundation of good health, everything else is secondary. Here are some tips for sustaining and improving your overall health...

  1. Vary your exercises: Make sure you hit all facets of physical fitness, including strength, cardio, flexibility, and balance. Experiment. Try weight lifting, running, biking, swimming, yoga, etc.
  2. Do what you enjoy: The best way to stick to a workout routine long-term is to focus on doing things you actually enjoy. If you hate running, you’re going to quit the first chance you get. Make staying in shape fun.
  3. Walk outside every day: Walking is one of the most simple and beneficial exercises that anyone can do. Allison and I walk for an hour every single day. And by doing it outside you also get the bonus of fresh air, sunshine, and vitamin D.
  4. Eat your veggies: We try to eat a portion of vegetables and/or fruits with each and every meal. So, even if you’re eating fried chicken or a burger, at least your salad will give you some extra nutrients.
  5. Don’t forget mental health: Make sure you keep your stress in check and your mind sharp. You can improve your mental health with meditation, reading, puzzles, relaxation, mindfulness, and physical exercise.

 

Hiking around Mount Hood in Oregon.
Hiking around Mount Hood in Oregon.


Travel


One of the best ways to expand your horizons and grow as a person is to
travel far and wide. Here are some ways to make travel even better...

  1. Go as far as you can: If visiting other parts of the US is as far as you’re comfortable, then do it. There are so many beautiful National Parks and landmarks to explore! However, if you’re able to, explore the far reaches of the world (especially when you’re young enough to have the energy).
  2. Be open-minded: One of the best aspects of travel is being able to see and experience how people who are different from you live their lives. Leave your stereotypes and preconceived notions at home when you travel. Embrace the differences!
  3. Get local: When you visit other countries, try to mingle with the locals. Stay with a family in an Airbnb, eat where the locals dine, and spend time just walking around the city streets, town squares, and parks.
  4. Try the food: One of the best ways to explore other cultures is through food. Always opt for the local favorites and specialties, and don’t be afraid to experiment.
  5. Explore the culture and history: Cultivate an appreciation for other cultures through their history, architecture, language, customs, etc. Exploring museums and going on free walking tours are great ways to learn more!

 

Exploring the views and ruins around Machu Picchu in Peru
Exploring the views and ruins around Machu Picchu in Peru.

 

Finances


When it comes to money, it’s easy to get lost in the weeds trying to figure out the best investing strategies and tactics for slashing expenses. Here are some things to focus on to make it easier…

  1. Automate everything: Set up automatic payments for everything: credit cards mortgage or rent, car payment, etc. Also, set up auto investments into your retirement and taxable accounts. Set it and forget it!
  2. Dollar cost averaging: When you automate your investments, you simultaneously use the strategy of dollar cost averaging. This removes the challenge of trying to time your investments.
  3. Simplify your investments: My favorite investment book is The Simple Path to Wealth by JL Collins, because it boils down all your investments to one or two index funds. We expand on this a bit by investing in a total of six funds, but it’s still quite a simple approach.
  4. Diversify: Make sure to diversify across and within asset classes. That means investing in stocks and bonds, both US and International. We also recommend adding REITs, precious metals, and good old-fashioned cash. If you’re feeling adventurous, you can dabble in real estate, your own business, and a small amount of crypto.
  5. Don’t forget the small things: It’s not sexy, but it’s important to pay attention to things like fees, expense ratios, taxes, and insurance. Keeping your eye on these expenses can save you lots of money in the long run.

 

FIRE Lifestyle


Once you achieve FIRE, your whole world is going to change. It’s crucial to be prepared and know how to make the most of this wonderful new lifestyle.

  1. Projects: Having projects to work on will ensure you stay sharp, engaged, focused, and inspired. Your projects can be big or small. For us, we keep busy with things like writing books, blogging, planning trips, and household projects.
  2. Connecting: Since you no longer have your built-in social network at the workplace, you have to make more of an effort to connect with others. Make plans to meet up (when safe from COVID) for coffee, lunch or dinner, walks or hikes, drinks, and/or general hang-outs.
  3. Routines: It can be helpful to create daily and weekly routines for your meals, workouts, walks, entertainment, and other every day activities. Our routines keep us grounded and sane, so we can focus on more exciting things.
  4. Get outside your comfort zone: While routines are good, it’s also important to challenge and stretch yourself. Try public speaking, learning a language, becoming a mentor, or anything that fulfills you (even if it’s a little scary at first).
  5. Own your FIRE: Many people feel guilty when they reach FIRE, because their friends are still working. Make sure to fully embrace your new lifestyle. You worked hard to get there, and you deserve to enjoy the fruits of all that hard work.

 

Allison showing off our 2nd published book, "Investing for Kids"
Allison showing off our 2nd published book, "Investing for Kids."


Work


In order to reach FIRE, we all had to work at some point. For most people, your working years are some of the most impactful and influential of your life. Here are some ways to make the most of that time…

  1. Don’t take it too seriously: Unless you’re curing cancer or solving the world’s problems, try not to let your work consume you. Keep your job in perspective -- you’re just crunching numbers, marketing a product, or building a widget.
  2. Embrace your work relationships: Some of our longest lasting friendships are with people we worked with decades ago. Just because it’s in the workplace doesn’t mean you can’t forge impactful friendships with your co-workers.
  3. Keep an entrepreneurial eye open: Many entrepreneurs start businesses based on products, services, or systems from the field in which they worked. It makes sense to leverage your current skills. I ran a successful side business for years using the online marketing skills I learned in my career.
  4. Take breaks: For your mental and emotional health, make sure to take lots of breaks throughout your career. This is everything from multiple daily breaks (take a walk around the block), to using your vacation days, to taking a sabbatical if possible.
  5. Don’t be afraid to jump: Many times the only way to get a promotion or increase in salary is to move to another company. I worked for 10 different companies over my 17-year career! Sometimes I got laid off, but other times I moved on my own to a much better situation.

 

Tough Mudder team
At one of the startups I worked for (BranchOut), we did a Tough Mudder race together. It was 95 degrees, 12 miles of hills, and 25 obstacles, but loads of fun!


Marriage / Romantic Relationship


One of the most important relationships you’ll ever forge is with your spouse or significant other. Allison and I have been together for over 25 years now, so we’ve learned a thing or two about making it work.

  1. Teamwork: Like any partnership, it’s important to work together to ensure equity. That means sharing the workload with household chores, finances, and projects. It helps to divide things up by expertise, skill level, and what brings joy and fulfillment.
  2. Check in regularly: I try to “check in” with Allison throughout the day to make sure everything is good. We have little pet keywords and phrases that we say to each other that just acknowledge the other person and let them know we’re doing well ourselves.
  3. Communicate (and listen): Men historically have a habit of interrupting women (as well as man-splaining things). I’ve tried to get better at this, but Allison still occasionally reminds me that I’m interrupting her or not listening.
  4. Cuddle: It may seem like a little thing, but hugging, nuzzling, and cuddling are important for your emotional and physical well-being. This can include physical bonding with your pets too!
  5. Say and show you love them: We tell each other multiple times throughout the day that we love each other. It’s also important to show your love by being considerate and respectful toward your partner.

 

Ringing in 2021 with a toast and a kiss!
Ringing in 2021 with a toast and a kiss!


Friends


It’s human nature to form bonds with others who have similar or complementary personalities and interests. It can get harder as you get older, but there are some things you can do to continue building strong friendships.

  1. Realize friends will come and go: Through no fault of yours or theirs, many friendships will wane over time. It could be that you moved away or your interests diverged. Whatever the case, just know that while some friendships will last forever, most won’t.
  2. Different levels of friendship: Not all friendships are close or deep, and that’s OK. You can be friends with your neighbor that you only see on your daily walk, or you can be friends with the person you went to high school with 30 years ago and only see at reunions.
  3. OK to discuss taboo things: Unlike family, which we’ll get to next, it’s usually easier to talk about racier topics with your friends (e.g. politics, religion, sex, etc). That’s typically because you’re on the same wavelength about these things. (Obviously this doesn’t apply to all friends.)
  4. Understand your friendships: Some friends need cheerleaders to encourage their dreams, others need guardians to steer them away from bad decisions, and still others just want to get together to have a good time. Know which roles you and your friends play with each other to maximize the relationship.
  5. Be a good friend: Whether you see your friend every day or only once in a blue moon, try to be a good friend. That means doing what you say you’ll do, respecting their time and values, and reserving judgment.

 

Tickle reunion
Another startup I worked for from 2002-2007, Tickle (formerly Emode, later bought by Monster), doing a reunion in 2019. I've stayed friends with these folks and many others from that company over the years. In this photo are founders from companies like Goodreads, Bebo, NFX Guild, and BranchOut.


Family


As an only child and with no children of my own, I come from a small family. Allison’s family is bigger but still relatively small with only one sibling. So, we try to cherish the few family members that are in our lives.

  1. You can’t pick them: You can select your spouse, but you can’t pick your family members. You get what you get, for better or worse. If you have a wonderful family, then lucky you. If not, don’t beat yourself up about it.
  2. Don’t take them for granted: While there’s nothing you can do about the quality of your family, it’s still good not to take them for granted. Unless they’re totally toxic, having family is usually a good thing. And remember that many people don’t have any family members at all, so maybe cut your meddling uncle some slack.
  3. Avoid politics: Unlike your friendships, it’s usually better to avoid antagonistic political conversations with your family members. Let’s face it, you’re not going to change each others’ views, so why put yourselves through the angst?
  4. Call out when necessary: Avoiding politics is one thing, but if you have family members engaging in reckless or harmful behavior, don’t hesitate to call them out. Being family doesn’t give you a free pass to be a bad person.
  5. No grudges: Life’s too short to hold onto long-term grudges, especially over relatively small issues. Unless it’s something major, let it go for your own well-being.

 

Hanging with the family
Hanging out with some of the members of our diverse, fun, and eclectic family.


Leisure


Leisure is basically what you do in your free time. How you spend this time can either bring you joy and contentment, or it can lead to stress and boredom. Use this time wisely!

  1. Read books: There’s nothing quite like immersing yourself into the journey weaved by a skilled author. Allison and I always have something on our Kindles to read at night (both fiction and non-fiction). One of the best resources available is the public library (good for e-books too).
  2. Get your culture on: Expand your horizons by taking in culture at art museums, theaters, science academies, zoos, planetariums, etc.
  3. Enjoy junk (in moderation): Don’t be afraid to indulge in mindless fun entertainment, as long as you don’t overdo it. We love hanging out at night watching TV (e.g., comedies, dramas, game shows), sporting events, and movies (e.g. sci-fi, thrillers, blockbusters, documentaries).
  4. Avoid conspiracy theories: While some junk is fine, don’t get caught up in all the latest conspiracy theories proliferating online. Developing good critical thinking skills is a must!
  5. ABC (Always Be Creating): It feels so rewarding to build and create things. It can be almost anything: artwork, a book, a blog, a business, a piece of furniture, or an entire house. 

 

Allison posing in front of this real cool and quirky painting at the Berkeley Art Museum
Allison posing in front of this real cool and quirky painting at the Berkeley Art Museum.


Life


Finally, let’s look at a few thoughts on life in general. Here are just a few ways you can make the most of the time you have on Earth…

  1. Have fun!: Life’s meant to be enjoyed and not taken too seriously. So lighten up, smile more, laugh a lot, and try to make other people laugh.
  2. Be adventurous: Don’t be so fearful. Go outside, talk to people, take trips, go on hikes, and get out of your comfort zone.
  3. Embrace each day: After my near death experience, Allison and I realized life was too short to spend on things that didn’t bring us joy and fulfillment. I try to be grateful for each and every day that I’m alive.
  4. Do good: Google’s motto used to be “don’t be evil.” You can make it your own life motto to “just do good” by giving freely, helping others, protecting the vulnerable, and generally following the Golden Rule.
  5. Love more: At the end of your life, what’s most important is how deeply you loved others and how much they loved you back. It’s like that classic Beatles song In the End: “And in the end, The love you take, Is equal to the love you make.”

 

Frolicking under a waterfall in the Caribbean
Frolicking under a waterfall in the Caribbean.


In Summary


Some people dread getting older and look at milestones like turning 50 with fear and trepidation. However, I very much look forward to this age in life. Why? Because I’m still (knock on wood) in very good shape, and since we FIRE’d, we have lots of time to make the most of the upcoming years.

Hopefully you will find some inspiration in these 50 reflections on life. These suggestions based on the experiences of our first 50 years on this planet have served us well so far. Feel free to use as many or as few as you like to enrich your own life.

As a friend recently commented on a post about getting older: Quam bene vivas refert non quam diu. Translation: "It is how well you live that matters, not how long." Here’s to another 50 years (or however many we’re lucky to have)!

5 Responses

  1. Jim Blankenship
    |

    Happy Birthday – and congratulations on making it this far!

    Your list is a great gift to all of us – we’re all on similar journeys, to one extent or another. Thanks for sharing!

  2. Amy
    |

    Happy 50th Dylin, great list!

  3. Chris @ Mindful Explorer
    |

    Happy Birthday and a great 50 reflections on the journey.

  4. Accidentally Retired
    |

    I love, love, loved this post. Really just great little tid bits on life and as someone in the midst of minor family drama and other parenting stresses its a good reminder about the bigger picture. Thanks!

    • dylinr
      |

      Thank you, so glad it resonated for you!