To Be or Not To Be: Ski Bum at 27?

Have you considered doing something that is more of a middle ground between the two? If I were in your shoes I would take a look at what job opportunities are available in Denver - can scratch your skiing itch on weekends and maintain everything you’ve accomplished so far in your career.

Don't have much advice to offer but feel you and think about this daily as another career grinding icecoaster. Hard to really take your skills to the next level when you are only getting 2-3 weekends in a year. 

Know someone who started a successful company now spends entire winter in whistler every year. Living the dream. 

Its getting so bad lately have been looking at SLC job postings lol  

fuck it dude, do a remote sales/biz dev job, crush it, make like 150k-200k and ski. all remote. u get tired after a year or two, do an MBA. yolo

Had similar thoughts once and sometimes still do. Ski towns get pretty quiet though and most locals only log about 30ish days a season (they tend to get really picky with conditions). If you can wrangle up like 2 weeks to head west and throw in some good Vermont weekends like this one, you might be pretty satisfied. 

Do it, you only live once. You won't regret the money, you'll earn it back. But you will regret never having taken this opportunity because once family gets in the way, you'll never be able to do it again. 

Get a job in SLC. 

Good fucking lord is the WSO mobile browsing experience broken. 

Anyhow, 

1. No, taking a step back at 27 is not an irreparable mistake. 

2. No, it will not be impossible to break back in with only 3 years experience. 

3. I can’t really speak about the friend/roommate situation. 

4. You would regret the experience if you run out of money. That’s really the only negative here. It may and probably will take you longer than you expect to get back in the game. 

5. Only if you like NYC women. There are hot women everywhere. There are cool women everywhere. You don’t need thousands - you need one that fits and has shared goals. If your goals aren’t NYC based, NYC probably isn’t the best place to find a girlfriend either. 

6. No. You should continue to embrace your hobbies. No one dies and wishes they worked more. I’m not dead and I wished I did my hobbies in my 20s more before injuries and life made them less likely. I’ve recently engaged with a former hobby I can do and it is incredibly fulfilling. 

7. I can’t answer that for you. 

Used to work in CRE in major coastal city, now live full-time in a ski town still working in CRE.  It's awesome.

I have a bunch of observations on this:

1.  If you want to dive all-in to living in a ski town but still working in CRE, the seats are quite limited, and I suggest you start networking ASAP and cast a very wide net geographically.  Many of the local operators are smaller operations of 1-2 principals + 1-2 analysts/associates so you'll need some luck finding an open seat, or you could also expand your search to things like homebuilders, brokerage, appraisal, lending, etc..  The majors RE assets in these towns are hotels, workforce housing, and shopping centers (office/industrial is mostly little mom&pop stuff or nonexistent) so start digging around on who the owners/operators are and make a networking list.
2. There will be a lot more job opportunities and opportunities that are more "institutional" if you do more of a half-measure careers change.  This to me would be something like:
   1. Working somewhere that operates in these towns, i.e. outdoor hospitality brands like Outbound (Waterton) or Field & Stream (Starwood), RE depts of Vail/Alterra/Aspen Ski Co/etc, CrossHarbor (owns yellowstone club + has portfolio around Big Sky), JMA Ventures, etc... Many of these towns also have shopping centers owned by major retail REITS.  This would allow you to at least do work and travel to ski towns, but you'd likely still be based and spend the majority of your time in a major city.
   2. Get any CRE job in a place like Denver, SLC, Bend, etc... again, you'll be spending the majority of your time in a city, but you'll at least have much better ski access than NYC.  If I were to move somewhere like Denver I'd still want a 2nd home in the mountains at some point though b/c skiing will be a 2+ hour drive during ideal ski times.
   3. Get a remote job and move.  This will be tough to do in CRE, but as others have mentioned will be more achievable if you left the industry for something like tech sales.

Overall, I think there are lots of ways to make a more ski-oriented career change without "throwing away" your career.  I'm at a small shop now, but still working on pretty sophisticated projects and feel confident my resume would still look good if I wanted to move back to a major city (although I may be restricted to applying to one of the hospitality/workforce housing places listed above to maximize transferrable skills).  In some ways I did likely "downgrade" my career a bit, but as you mentioned, if the end goal of a highly successful career is to move to a ski town, why not just fast forward and start now?

Literally was thinking about quitting to be a ski bum earlier today too, but decided against it because I have too much shareholder value to create

Wow, lots of thoughts here. A few years older than you. I don’t share your passion for skiing, but I’ve faced similar choices regarding career/lifestyle.

First, I’ll say that I think you’re right to look to move out of New York. In my experience, the people who stay there long-term are those with very strong career aspirations and/or personal ties to the city. Why stay if you’d rather be somewhere else?

I may be off-base here, but if skiing is truly your passion, why don’t you look into a career directly related to the ski industry? Rather than having a 9-5 and spending your free time on the slopes, why not integrate the two? This could be, but doesn’t have to be, real estate related. I would think that the 9-5, if unrelated to skiing, could start to feel like a chore.

If you’d prefer to keep skiing but not make it a career, I would echo what Ozy has said. The reality is that our hobbies have to take a backseat. But you can find ways to fit that hobby into your life. Maybe that’s moving to Denver and skiing on weekends.

Finally, I would say to be patient and really think this through. Looking for a job when you don’t have a job sucks and I strongly do not recommend it. Don’t be afraid of intermediate steps. For example, taking a real estate job in Denver where you’d have better access to the real estate guys in ski towns and easy access to ski. When you’ve broken in, you’ll be in a better position to land a job that checks all your boxes. A local network is a game-changer.

It will all work out. Best of luck.

Could balance both. Maybe there is some chill corporate finance gig at The North Face, their offices are in Denver. 

I would recommend you explore relocating to a mountain/outdoors focused market like Denver, Salt Lake, Reno. Work/life balance in these markets with strong consideration for the ability/flexibility to take time off after a major storm, get more days/take more time off in winter is much more normalized and acceptable than a grind and hustle market like NYC. Like others said, I think you can keep a job and build career experience while getting your reps in, if you make the geographic location. 

At the end of they day, if that still sounds like too much of a compromise, go for it. Just understand it will be more difficult to jump back into the industry when you are ready in terms of explaining the work gap, competing with younger folks for the same positions, etc. There is nothing wrong with that, provided you temper your expectations accordingly. 

I aint reading all dat. Good luck

You're a 26-27, financially independent grown-ass man. Your parents don't have a say unless you let them.

You don't have any major responsibilities; you're at the prime of your young adult life and have the resources to do it. You've worked hard and earned it. As others have said, you're not destroying your life or career. And the easiest place to find a woman who loves skiing as much as you is a ski town, not necessarily NYC. It's worth strongly considering. It might be the greatest time of your life.

Backflips are easy bro you can 100% do one this year. 

Some tips: 

Practice a ton on trampoline. 90% of it is feeling comfortable in the air. IMO any trick you can stomp 10 times in a row on a tramp you can do on skis. 

Don't spend years "waiting to build a jump on a powder day". Not saying you said that but have heard that refrain a lot. its not going to happen. You don't know how to build a jump and if you do try, the jump is going to suck nuts your first couple times. 

Find a nice medium park jump and just hit it a bunch. Do 3s or whatever tricks you have just lapping it until you really feel comfortable on it. IMO a slushy sunny spring day is ideal to learn. 

Learn on a sunny day with a clear sky. Flat light makes it wayyyy harder to spot your landing. 

I learned a bunch of tricks when I was you by making a pact with my buddies that if you day youre going to attempt something and dont, the other guys get to wail on you at the bottom. Good commit motivation haha. 

Just do it tho its fr not that hard.   

Thank god I live on the west coast. 

Have you been able to ski local east coast mountains this season? After a particularly good ski experience at the end of last season I became obsessed with skiing again and considered a move to Denver. Skied often growing up so it’s one of my top passions. 

I didn’t end up moving last year and I’m still in NYC but I did find the Ovrride bus. Gotta shill it since it’s so easy to do day trips with them. The bus picks you up really early in the morning in the city but you get to the slopes around 9 and get back on the bus around 5. Back in NYC between 7-11 depending on the mountain, so it’s an all day commitment but only for one day of the weekend. I’ve been doing it most weekends this season and if you have either pass it’s a no-brainer easy way to get days in. They do a fair amount of the major east coast mountains. It’s been just enough skiing to supplement my typical one longer trip per year without feeling like I need to move.

I would suggest you try to get as many days in as you can for the rest of this season / next season while hunting for real estate jobs in Denver / SLC. You might find you can reach a sufficient level of skiing here, but if not then definitely worth looking seriously for a new job. Unless you take a terrible job / go broke I don’t see this as a huge risk because you’re still in your 20s. Plenty of time to try something bold now and still course correct in a year or two if it’s not what you expected. Only you can place a number on how much you’re willing to sacrifice to be in a ski town. Certainly possible that a lower paying, less prestigious real estate adjacent role is enough to pay the bills and that might be good enough for you. I think it’s worth exploring if you feel this strong of a pull to the mountains. 

Have also though seriously about how to live in a ski town sometime in the next couple years, but I enjoy my seat too much to leave New York just yet. Golden handcuffs / hours too good. Always trade-offs. Good to keep your health so you can ski seriously well into your 70s and 80s. Absolutely agree it’s better to ski hard when your body can still take a beating. Good luck with it man hope you stomp a backflip. 

Its pretty hard to break into a real estate job right now. I have 4 years of experience and have been unemployed for 8 months. And this is even keeping my previous job on my resume open because they use me as a consultant from time to time. 

I am pretty much a ski and surf bum now since I live in LA and grew up doing both growing up in coastal SoCal. I am way more stressed about finding a job and would rather have one right now then go surf every morning like I do and go ski during the week with the meager funds I have left.

Others have said this but you can definitely find a middle ground here. Denver and SLC are obvious choices, but the other west coast cities are all close enough to great skiing to easily get out there for a weekend on a consistent basis. LA, SF, and Seattle are all a manageable drive from sick mountains and massively expand your job prospects.

My two cents is this seems like a "chop off the head to cure the headache", approach when a more balanced approach would work. 

Maybe try starting with some more minor changes to your life as other have suggested here, worst case you can still quite your job if your still not happy. 

Im in a similar boat as you. I have been working 2 years in NYC and have the same thoughts of finding a remote job and living in a ski town. Why work hellish hours in NYC surrounded by people who are beyond miserable and are all just chasing money? 75% of the people I work with have zero interests outside of work and just work around the clock 6 days a week, how will there life ever be fulfilling?

Some thoughts - I think that our parents generation in general is going to be more inclined against a move like this. Most of them are much more "career" oriented and just view that this will have a negative impact on your career. I feel that there is a large group today of 20-30 year old post-grads are much more inclined in pursuing personal interests alongside a career, or hell some just straight pursue there interests. In short, I think that your parents view is certainly tainting your perspective and making you hesitant to make a move like this.

I also think that 75% of the people on WSO and some providing feedback here (I think most of the feedback here is super good tho) are people who truly identify themselves by there job. The kind of people that you would ride a charilift with and one of the first questions they ask you is about what you do for work. The kind of people that define themselves and others by what they do, while people like yourself and I are more inclined to tell people about skiing and other things we enjoy and not just talk work. Funny short related story -- good friend of mine who I met in my time living in a ski town was riding the lift with some F500 CEO and my buddy was straight ski bumming washing dishes at night and charging 7 days a week. The CEO asked my buddy what he did, and he said what I described above and the CEO said something along the lines that he would trade his whole career for what my buddy had if he could go back. Deep down what really matters? Is it grinding your ass off to do something that doesn't excite you to make a ton of money one day and retire at 60 and then not even be able to shred hard? Or, say F it now find a new job in a SLC, Denver, San Fran and go to Tahoe on weekends or just go full remote and live in a ski town. 

I think the biggest thing is finding the balance. Lets face it, we both work in Finance and are certainly somewhat motivated by money (skiing is expensive AF right). I think it is really about finding the balance that is the most important. Where can I find a job that lets me ski weekends? Sneak out for a few laps on pow days,?etc. If you find anything along the likes let me know, and I would be happy to do the same. Send me a PM and we can chat too

Such an obvious solution here that I can’t believe you didn’t mention. Find a CRE job in Denver or SLC. Real cities with real jobs and plenty of dating opportunities yet very close to the mountains. Heavy ski cultures too so easier to find a woman with aligned interests.

Utah is a great option - SLC is 30 minutes away from 4 top ski resorts and you can find a finance job that only works you 40 hrs a week with relatively good pay. 

If you love skiing so much how are you only getting one trip a year in?

I moved from a big city to a smaller one for work and my office is exactly 20 minutes from a ski hill so I’m able to go straight after work with my ski gear in my car (and change into my base/thermal layer before leaving the office). Still get to work in corporate and hit the slopes 2-3 weekdays each week. As others have mentioned, you can find balance!

I just got hit up by HSP for a REPE opp in Denver lmk if you want the email on who I got it from

Hey man, Manna Tree (LMM PE w/ Health food focus iirc) has a position open in Vail CO right now. Literally in the resort mountain base of one of the best ski resorts in the country. I don't have any further color on this position, but I saw it by coincidence and thought of this post.

Sounds like it could be a home run for you if you can hack it a bit longer. Best of luck!

https://www.linkedin.com/jobs/view/4167575855

I know PA or upstate NY isn’t exactly Aspen but I know a lot of guys in their 30s who have PA or upstate NY weekend houses where they get urges like this out of their system. I’d rather unload an AR-15 off a mountaintop than ski down it so I’m more inclined to buy in PA but this is a way more attainable goal in the near to intermediate term than getting that $30mm beach house in Montauk (which I would gladly trade my gun rights for). 

I did 6 ski seasons after high school (Canada, NZ, Japan) and that’s literally how I broke into industry. Ski instructing teaching CEOs and bankers all day. In structured finance now and would say skiing has helped a ton to get in the industry and bring outside perspectives. Like on those interviews it’s so easy to talk about skiing the whole time so they never grill you at all. Also helps if you do some ski racing/comps too, even if you’re not that good. That way you bring that athlete competitive mindset in the office, makes coaching and leadership skills easier too bring out. All I would say is 100% do it, but don’t be a dishwasher or do some mindless job. Do ski instructing because the network is unmatched to get your next finance gig. Especially if you start teaching private lessons. The only people that can afford them are big time Bankers, tech or PE hedge fund types, and you basically get all day to network with them and they buy you lunch and tip you $300 per day