Advice - promotion/side hustle/surfing/traveling


Hey everyone,

I’m going to ask a question and the answer will probably be “do what makes you happy.” Nonetheless, I’m going to ask.

So my current situation is that I took a year off in 2016 and lived abroad volunteering with Doctors Without Borders in South Sudan helping run hospitals. During my holidays I would surf and surfed in Costa and Bali. I found out I really enjoy surfing even though I’m pretty bad.

I wanted to move back to the States because traveling full time is not my cup of tea (at least yet). I came back to the job that I had when I left, a series of fortuitous events occurred in my favor for this to happen.

From a financial standpoint: I make $100k+ and save 25% of my income. From a savings perspective I am in the $200k range. I am 31. I also started to do some side consulting and picked up my first client for roughly $3,500 a year. I can pick up more but I just don’t have the time right now.

On the personal side: I’m single and have no children. I just got out of a long distance relationship so focusing on doing a good job at work and traveling/surfing.

Why I love my job: I have a great team and I get 2 months off each year. 1 month is unpaid. This allows me to travel extensively and take long surf trips. I am currently in Costa working remotely.

The dilemma: my boss (the CFO) is quitting in June and has asked if I want to apply or not. It would be a big raise and I’d be a young CFO (ego talking here) but I’d lose the ability to travel 2 months. I’d be back to 2 weeks of vacation pretty much and that is not something I want.

Yes I could be the CFO save up a ton of money and then retire sooner but the trade off would be giving up the best years of my life when I most physically fit (training for an Ironman) to possibly not even make it to 40. My cousin who is my age just got diagnosed with breast cancer. She is young and is in great shape too. Another thing I consider is that when I talk to people, I rarely bring up what I do at work and try in earnest not to ask people about their job - your job rarely defines you. I talk about my surfing/traveling and the people I’ve met doing both. I enjoy my job but it is not my defining characteristic.

What would you do?

My answer is that I think I’m going to decline applying to be the CFO and maybe just take on more clients for my side hustle consulting.


What I would do and what I should do are totally different things.

I would take the CFO job with the idea that I would be able to retire that much sooner even though I know it’s probably the wrong decision.

You’re in a position to be able to travel the amount you’re comfortable with, you enjoy the travel you undertake, and you make a comfortable enough living while being able to save a significant portion of your salary. If you’re more or less already living the life you want, why change? What would you actually gain from making more money and being able to travel more 10 years from now if you’re not even certain you want to travel more?

My advice, which is worth, at most, what you’re paying for it, is to skip the CFO offer.


Hey Surf!

Heres my 2 cents…

If you take the CFO job that is a commitment you are giving to the company…not just a job you can quit a few weeks in if you don’t like it. From what your past sounds like, you enjoy freedom. Just because your ego is pushing you doesn’t mean you have to take a job your gut is telling you isn’t a good fit for who YOU are as a person. Would it be enough for your ego to know that you COULD have been CFO if you wanted but chose a different route because you had the option? Sometimes we have to talk our minds into what out bodies already know. As you wrote in you last sentance…

Someone who runs a company (or a top portion of it) spends quite a bit of time dedicating their life to that business which in turn then somewhat defines them. Think Jeff Bezos and you automatically think Amazon. Apple and you think Jobs. When you are at the top, you are what you do… Who do you want to be?

Good luck with your decision and keep us posted!!


Lol I’m working right now so that’s how I can respond so quickly. Just had a great morning surf session. Anyhow, very well said @MissMazuma

And yes you are right on taking the CFO job. It’s a 5 year commitment. Obviously it’s an at will employer but loyalty and my word are very important to me (odd coming from a Millennial I know).

Yeah, my gut is telling me it’s the wrong thing to do. My worry is the new CFO will be my boss and they might not be keen on my current remote work situation. I guess I should talk to the CEO about it.


Ouch - 5 year commitment? No. Definitely no. Life is too short to be slave to a position. You have an amazing skill set that you can use all over the world. Don’t limit yourself for the benefit of a title. If the new boss wants to shackle you it is possible you might have to make some other decisions in the future, but regardless, it sounds like you will find a way to float to the top. :slight_smile:


I left the corporate world a few years ago, and while I still work part time, I definitely wouldn’t go back to the crazy hours and having to manage people and teams. My time is far more valuable, and you are fairly well off financially for your age. I would suggest you try to get a job at Patagonia… they actually let workers take off when the surfing conditions are good! :slight_smile:

Also, I love that you can get 2 months off. I wish companies would off unlimited time off that people have to “buy” or go unpaid.


Lol I read that article as well about Patagonia. If it were in Texas, I would. I want to be close to my family as my parent’s are aging - my mom is in her 70’s. Also, my cousin has breast cancer so I want to be close to her. Maybe I’ll look later on but right now, staying in Texas is important to me.

Not all of the 2 months is paid time off - some is unpaid but I’m okay with that.


I would apply and negotiate for the benefits you want. If you are really qualified for the position and they offer you the job, they clearly value you as an employee. Most companies will do almost anything to keep a good employee on board.

Demand at least 1 month vacation each year, if they reject, propose a reduced salary in exchange for the vacation (whatever the extra time is worth to you). Work it for a year or two, then re-evaluate.


Possibly inaccurate observation:

The fact that this whole thread has gone by without discussion of how big the raise would actually be, indicates to me that the money isn’t very important to you.

Personally, depending on how large the raise is, I’d strongly consider taking the position, gutting it out for 5 years, and saving and investing like a maniac to reach complete financial independence before I’m 40.

Probably much easier said than done.


I know what I’m going to do now. I’m not willing to sacrifice my happiness today for more money. I have enough and that’s all I need. I don’t want anymore time off than the 2 months that have been granted to me so the whole early retirement thing isn’t for me - I figured that out in 2016 when I traveled for a year. Call it fortuitous timing but this article arrived in my inbox today. I am very lucky to have an amazing and fulfilling life outside of work. I have friends all over the world and I have the funds and time off to see them. I get to do things I love like train for an Ironman and live in Costa Rica part time to surf.

Thanks for your comments everyone.


It’s a simple yet profound question to ask yourself "What’s important about money to You?"
When you align your financial choices to what’s important to you, not only will you fast track your progress to achieving your goals sooner, you will also be more present along the way!
Keep in touch bro!
Living the dream!