I snowboard every day. Whenever I want to, for whatever reason, I can put on my clothes, walk over to the chairlift, and take a few runs.
I don't mean to say this purely as a brag (although lets be honest it totally is). I mean to say it more as a "hey if you really want this sort of thing, you can totally get it if you're willing to do all the right stuff."
In fact, it wasn't always like this. After I graduated college, I moved to a mountain town and worked as a snowboarding instructor (much to the chagrin of my immediate family).
Don't get me wrong, it was a really fun job, but let's be real. It's not going to fill up those investment accounts or propel you to financial independence anytime soon. It's also not the most intellectually engaging sort of work. If you're more of a creative type, you'll eventually get bored with it. Ski coaching is a job best done part-time.
In any case, most ski bums burn out really fast because they can't make nearly enough money to pay for all of the expenses that come with the lifestyle. It doesn't help that so many of them are young and have terrible money habits. They spend night after night racking up bar tabs, and then a single injury wipes them out completely.
After mom and dad scrape them off of the mountain, they have the mother of all heart to heart conversations. The kid promptly shaves his beard, cuts off the rad mohawk, and then goes to work at the family car dealership. The circle of life continues.
But this doesn't have to be you, and it certainly wasn't me.
Although I was (and still am) a ski bum, I was more the enterprising type. When others were out partying, I was devising Internet Money Schemes. Eventually, one of them actually worked, and I used it to kickstart my freelance software engineering career.
So here are a few things I learned along the way. Hopefully you can use them to get whatever flexibility you want out of life, even if skiing isn't your thing.
I can attribute most of my current flexibility to being good with money (which I can by extension attribute to my spouse who taught me these skills). I remember one summer where I spent every day working at a restaurant on the mountain, making much less than what I make now. At the end of that summer, I had saved up $5000.
At one point, I let this fact slip in conversation. My co-workers were blown away. "I don't know any 25 year old with $5000 in savings," one of them said.
To me this was kind of crazy since $5000 really isn't that much money (especially for a 25 year old who probably should have started saving much earlier). If you have any kind of emergency like a job loss or an injury, you're going to need something to fall back on. Many people get wiped out because they have no savings whatsoever.
This habit came to be pretty useful several years later when a freelance project would end and I'd need to find the next thing. It's so much easier to search for work when you aren't stressed about paying your bills. This cushion is what keeps you in your cozy little mountain palace, tucked away from corporate America.
It may surprise you to learn that the first dollar I made from software came from entrepreneurship. One of my side projects sold over 500 units in a day, and it opened up a steady stream of passive income that continues to pay me. I used this success as marketing and was able to get remote contract gigs.
But as we all know, income sources can dry up. Industries change. Fads come and go. One day, native iOS development is all the rage. The next day, companies get tired of paying for native iOS plus Android development. They start shifting towards technologies like React Native and Flutter (we can debate whether that's a good choice or not but there's no doubt they feel the burn), and bam you're out of a job.
In the software world, your value and marketability can drop just like that. It's okay. You're still a great developer! It just means you've got some catching up to do before you become gainfully employed again.
If you have multiple sources of income, it's okay if any one of them dries up. If I lose my job as a native iOS developer, I can fall back on tutoring gigs, working at the ski resort, app sales, freelance writing, dividends, and stock appreciation (or maybe I just wait it out and take a much-needed snowboarding break 😁).
Even with all of those potential sources of income, I still feel like I need to keep building more. I should release more apps, maybe start a YouTube channel, and begin picking up different programming languages so I can do a better job of pitching myself to the next client.
Having a plan B, plan C, and plan D are what keep me snowboarding every day in the winter (and mountain biking in the summer). I don't stress because I know that no matter what's going on, there's always a buck to be made somewhere.
I know exactly how much money goes in and out of my life. That means when I say "save six months of your income," to me that means keep a spreadsheet with all of your expenses, calculate that amount, and keep it in your checking account as a baseline cash position no matter what.
It really helps to be frugal. Lots of people think it's super expensive to live near a ski resort, but that's not totally true (especially if you have a software engineer's income). I spend around $25K a year for everything. That includes housing, health insurance, food, entertainment, ski passes, snowboarding gear, you name it.
I also do many things other ski bums aren't willing to do. I take the bus whenever it makes sense to do so. I don't go to bars. I eat out occasionally with the spouse but don't make a big habit of it.
I get deals on my snowboarding gear, and I don't feel the need to keep updating my wardrobe every season. My jacket and pants have lasted five seasons and probably need to be replaced right about now (hint hint sponsors - I still hit jumps and rails).
Since I work remotely, I never have to drive into an office. I own my car outright, pay the minimum insurance, and drive it as little as I can (you need to drive them roughly once a week otherwise they start going to hell pretty fast).
It helps that we don't have kids but I also don't think kids would necessarily be that big of an expense if you're pretty smart with your money. I do have a nephew who I plan to lavish with plenty of mountain goodness if he's into that sort of thing.
Food can cost as little as $3K per year if you buy raw ingredients and avoid most pre-packaged foods most of the time. Add in a few Costco runs and you can probably save an extra thousand dollars a year if you want to. It all depends on how much effort you want to put into saving. Sometimes it's not worth the effort but if you've just lost your job, you're time rich and can therefore afford it.
Either way, my habits are pretty simple and thoughtless. Once you start building them, you can just put your brain on autopilot and stop worrying about spending your money because you probably won't be doing anything all that crazy with it.
If you follow the third rule and you're working as a freelance software developer, chances are you're going to get a surplus of cash. Don't let it sit in a checking account! Invest anything over your six month cash reserve.
I happen to be in Vanguard ETFs that I invest in through my Fidelity account, but you can go into real estate or any other asset. No matter what, always fund your Roth IRA.
I can snowboard whenever I want to because I have built up the ability to say no to controlling clients and situations. Most of my clients are awesome and encourage what I do, but some folks just aren't of that persuasion.
I've had clients who expect you to answer all communication within minutes or who spend hours and hours on the phone discussing nothing of importance. If you're smart with your money, you can politely say no to this sort of thing.
I have some simple and straightforward rules. All meetings need to be scheduled in advance. I work remotely and can come into the office occasionally if you're willing to pay for airfare etc. I work my own schedule unless there's something high value that we need to collaborate on. Also, I will work weekends if you can persuade me that your business has quite a lot to gain from that effort.
Most of the time, I work between 30 and 40 hours a week. Sometimes I work more than that, but it's pretty rare. I almost always work on my own schedule, which is how I can go snowboarding in the morning while working the afternoons and evenings.
A well-funded ski life is certainly within reach if you're willing to work for it. You just need to have a backup plan and become more aware of your financial situation.
Even though I live at the base of a ski resort, I am still able to save roughly 50% of my software contracting income. As each year passes, I get that much closer to financial independence. In the not-too-distant future, I'll be able take only the contracts I want while focusing on my own revenue generating businesses or just saying "nah" and doing more snowboarding.
You can do this too.