When I was a poor undergrad college student I set an important financial milestone for myself: I wanted to be able to afford guacamole.
Others (myself included) chuckle when I talk about that now. But there is definitely a kernel of truth to that statement.
I remember vividly being a student trying to work enough hours at my part time campus job as a building maintenance worker that I could afford tuition, groceries, rent, school supplies, and gas for my old beat-up 1998 Honda Civic. At that time in my life an extra $3-5 on an expense felt like a significant purchasing decision.
My solution to this was to eat as cheaply as I possibly could. I bulk purchased ingredients from Costco for basic meals like spaghetti or PB&J sandwiches with roommates to help the dollars stretch further. I’d scavenge extra groceries from my parent’s pantry when I occasionally visited (with their permission of course). And I got extremely familiar with 100 different ways to eat instant Top-Ramen and love it. But when I wanted to treat myself to a luxury, I would go to Taco Bell.
Taco Bell was the ideal splurge category. Not only was it Mexican food (my favorite) and closely accessible at the local cafeteria, it was most importantly the cheapest fast food on campus. It was the perfect pick-me-up after a hard day, or a way to reward myself for doing well on a test or major class project. I knew the menu so well that I knew exactly what $5.39 cents would get me (2 crispy tacos and a beefy 5-layer burrito), and I could safely spend that once or twice a month on my measly budget.
Whenever I’d be in the Taco Bell line I would look longingly at the other items on the menu and long for the day when I could purchase them without worrying about blowing up my budget. Guacamole was the epitome of this. It was such a small thing (maybe $1 extra at the time) to add to a meal. But whenever the cashier asked me if I’d like to “add some Guac” I’d sigh, and say no because I felt like I couldn’t afford it.
That is when I decided that one day I was going to become “Guacamole Rich”. I determined that having the ability to add those small little add-ons for myself at a restaurant without a second thought to my budget would be when I knew that I had made it financially. It became the new measure of success.

When I think about that today I can’t help but smile a little. While I’m not overtly wealthy by any means, I have a great job/income and it has been many years since I’ve worried about ordering guacamole (something I take great joy in when I go to Mexican restaurants). I don’t remember the last time that I truly worried about ordering an extra side while at a restaurant. As charming as that sounds, there is a more important principle at play: having small but simple “lifestyle” milestones are important for our progress and happiness.
Whenever we think of growing our careers, we often tie the definition of success to big things like a title change (ex: “When I’m a VP”), salary increase (ex: “Why I Make $150K/yr), or even destination (ex: “When I finally work for McKinsey…”). Those can be useful metrics in and of themselves, but there is also danger to tying our happiness to major things. As a personal example, my wife and I have always dreamed of building a modest sized dream home one day. After pricing it out recently, we realized that this is something that we can (and will) do, but it will likely take several more years of saving than we’d originally anticipated.
That’s the trick with big milestones like a significant purchase or promotion, the gaps in time between them tend to be large. But instead if we set very small “lifestyle improvement” goals for ourselves we can find a great deal of delight along the way. This can be as simple as realizing that you can now afford that $1 guacamole with your burrito. Many of these goals don’t even need to be financial. They can be as simple as getting into a position at work that you can leave for home at 5:30pm instead of 6pm and treat yourself to a regular extra 30 minutes of personal/family time.
In fact, I would argue that finding a regular supply of small and simple ways to improve your day-to-day life is one of the best ways to enjoy the journey. The beauty of this approach is that many of us are already “guacamole rich” without even realizing it. We likely can afford that very minor purchase (whether financial or time) already, but have allowed our “saver” mentality to get in the way of acting on it. For example: after years of putting up with a pair of used shoes I finally realized that I was being silly about penny pinching and just bought myself a brand new pair of quality (but inexpensive) shoes. I feel a little bit of satisfaction every time I put them on.
The point of all of this is not to encourage spending you can’t afford. I’m a huge proponent of wise financial planning, saving, and investing. Likewise, I’m also an advocate of “working hard now to play more later”. But I’ve also come to realize that sometimes that mentality can go a bit too far. We all need to (as my wife reminds me) find joy in the journey, and not just fixate on the big destinations or milestones. Small and simple lifestyle upgrades are a great way to do just that without jeopardizing your career or your bank account. And in most cases, you’ll find that you’ve long been in a position to stop living below your privileges.