If I Knew Then…

Two weeks ago, I suggested that a college student get a cheap trial membership to a gym.

“How cheap is cheap?” she asked.

“Like 30 bucks,” I said. “Maybe $45.”

The look on her face said it all: That’s not cheap… and 45 isn’t the same as 30.


I get it. When I was in college, spending close to $50 to use the free weights was not part of my budget either. Being a student requires far more creativity than that.

“OK, how about this,” I said. “Go to the gym down the street and ask for a free week-long trial. Then, the week after, go to a different gym and do the same thing. You can probably get through most of the summer that way.”

You best believe I pulled that shit during my first winter in New York.

“If I can give you some unsolicited advice,” I continued, because no one asked me to. “Don’t stress about $30. One day, not so far from now, you’ll be making money and when you look back, you’ll think it was silly that you didn’t spend that little bit on something important.”

Of course, not everything you want while you’re in college is “important”. Drop $30 on new shoes and a few cocktails when you don’t actually have the money and you’re on your way to some substantial credit card debt. But for things that actually add value to your life, contribute to your health or keep you safe, I wouldn’t cut corners. Take a cab after midnight; go to the dentist; sign up for a yoga class. You’ll be glad you did later.


That got me thinking. If I wish I had the good sense at 21 to care less about some line items in my budget, what am I doing today that I’ll laugh about ten years from now? It’s an especially interesting question since I can, at this very moment, go anywhere and do anything. I have the rare combination of income and mobility with no real responsibilities to hold me back. If I have regrets later, I’ll be fully at fault.

Here’s what I came up with.

1.   Spend better.

Once again, I think one of my biggest regrets years from now will be that I skipped out on things that I deemed “too expensive.” I didn’t take a helicopter ride or glacier walk in New Zealand. I never ordered caviar in France. I didn’t try windsurfing in Madagascar. Just last week, I talked myself out of a trip to Tanzania even though I want to hike Kilimanjaro. “That’s too much,” I decided, even though the trip is probably only going to get more expensive – not to mention more difficult and more inconvenient. The time for me to do things is now, so why aren’t I doing them?

But the thing about budgets is that if something goes in, something else has to come out. If I want to try cross-country skiing in Finland, how should I offset the cost? The first answer that comes to mind is “Food.” But that won’t work, mostly because I don’t spend much on that anyway. My real Achilles heel is convenience: I take an Uber when the bus will do. I use a car service when I have an early morning flight. I sometimes book an airport hotel just to save myself the trouble of sitting around during a 12-hour layover. Those things make life easier, but they don’t make it any better. When I look back, I’m sure I’ll remember the surf lessons in Indonesia, but I won’t care about the driver I hired to take me to Ubud. Long story short: I can stand to prioritize my budget.

2.   Go further.

When I started this trip back in February 2016, I had some pretty strong feelings about my list of destinations. “I didn’t quit my job to go wander around Europe,” I often snipped. This, of course, turned out to be hilarious for two reasons: 1. I didn’t really quit my job. 2. I’ve been bumming around Europe ever since – mostly because it’s easier for me to do my job here.

I’m not complaining. I’ve enjoyed almost every single place I’ve visited during my travels. I went to more than 40 countries – some remote, some not. I still made stops in Madagascar, South Africa, and Indonesia, but I haven’t been to Thailand, Vietnam, Chile or Colombia like I originally planned. What’s worse, I’m not even entertaining the idea right now because they’re places that require a modicum of extra effort: I’ll need a visa; I’ll have to brush up on my Spanish; There might be bugs.

I’m comfortable where I am. And that’s a shame. Because hardly anything great ever happens when you’re comfortable.

3.  There is no worst case scenario.

When I’m anxious, people often ask: “What’s the worst that can happen?” And that’s a terrible thing to say to me, mostly because I already have a few ideas and they seem even more believable once I say them out loud.

The thing I’ve realized over the past year isn’t that things won’t go wrong – it’s that even when they do, they’re hardly ever as bad as you imagined them to be. Lost luggage can be replaced. Missed flights can be rebooked. Stolen passports can be reissued.

I worry less than I used to, but I still waste a lot of time and energy coming up with a mental list of things that probably won’t happen. I need to retrain myself to not think in terms of “the worst case scenario” – preferably before I start taking the bus in some of these far flung destinations.

I’m sure there are other things I’m doing that are pointless, misguided or just plain wrong. So. My question to you: What habits, if any, have you looked back on and laughed about? What’s your “If I Knew Then…” list? Having gotten to know me through my blog, what unsolicited advice would you give me?


  1. What you are doing now, is finding out where your edges are, mentally and physically.
    You are basically fearless, which does not mean witless, because you do have that sense of “oh…maybe not…” for whatever reason.

    Unsolicited advice? What you gave that girl, about the wisest way to spend that $30. Turn it around and look at it from your viewpoint, and I think you’ll see you’re doing the same thing yourself, and joyfully.

    And that’s the key, lady. Joy. In twenty or thirty or even forty years you may not be able to climb those mountains (or even want to), or whiz all over the world…but you have all the memories. And that’s really all we are, is what we remember. Right now is here and gone, a spark in the sky. Memory is what we all end up with.

  2. My hard-won wisdom is that comfort is the ultimate dream killer! I can’t even count how many dreams, aspirations, or goals I haven’t pursued in the interest of comfort. It’s a work in progress…
    (I love your blog. I’m so glad I found it!)

  3. Well, you did ask.

    People. Perhaps you have a vibrant, active social life but you do not mention it on the blog for privacy reasons. OTOH, I get the feeling you are a bit of a loner. Live what makes you comfortable – most of the time. Take advantage of all the cool places you go to get out of your comfort zone. (If you were a social butterfly, I’d suggest the reverse.) In each place you go, set up an appointment with a person in your industry or hobby. Offer to buy them lunch. In return, have them talk about how X is done in their country. Everyone likes to talk about themselves & their job/hobby. Not to network, or for profit, simply for the pleasure of meeting new folks & learning new things.


Leave a Reply

Your email address will not be published.