Pushing Pause — Planning the Jump

Brian Huy Mac
7 min readDec 15, 2021


Original Post: January 7, 2019

Crap… when I hit publish on this note I am publicly committed…

Better Questions = Better Answers


So I am sitting here writing this post a little scared, ok more like terrified but I am hoping by the time I am done I’ll be excited as hell! Let’s rewind a little as in previous posts I have talked about how I set a # Hastag as a theme for the year and then break into goals around the HWL (Health, Wealth, Love) framework as part of my planning. I originally thought this year’s theme was going to be #FAILFAST kind of try more things outside of my comfort zone, fail more, but recently after starting to read “Questions are the Answer” By Hal B. Gregersen I began asking myself how do I reframe my theme not as a statement, but as a better question? Essentially how do I push myself to make a jump? Overcome the fears with decisions, especially very big ones about career, where you’ll live, etc.

Friends in BALI :P

For a very long time an idea has lingered around — how could I do even more traveling / exploring? How can I find ways to contribute more? Not just a 1 week, 10 day surf trip here and there, or a weekend when I am somewhere for work, where things are already planned , hotels / accommodations are already booked. I have a few friend’s who have jumped into the “Digital Nomad” lifestyle and I am not entirely sure I want to go in that direction, but they have definitely planted this seed of how do I reduce some of the restrictions to going on an extended adventure?

BUT, here’s the BIG BUT, Life is good…like really good right now…

I am in a great challenging job, it gives me lots of opportunity travel, mentor others, and pays me very financially well, along with I get to live in Santa Cruz across from the beach in California. I have a great group of friends/support in California. There’s this fear of losing all of this. I am in the US on a work visa which adds another layer of complexity factor — goodbye status. It’s not like I haven’t been thinking about this for awhile, and before people go how can he afford this: I’ve been saving money and points the last 3 years towards some sort of big trip. Yet, the Lizard brain of fear starts kicking in… well what if I just take a 3 week vacation? maybe a month? 2 month sabbatical? this way I can come back to my job, life, toys in Santa Cruz…

Back to reframing questions: What do I want to get out of an extended adventure that I can’t do just taking a few weeks or 1 month? It’s not like I am trying to escape from anything, somehow I was lucky to stumble on this TED Talk via 1sec Video App (Fun goal this year to document / grateful for year events) blog


What really stood out for me was this concept that we learn for 25 years, then work for 40 years and then retire at 65 for 15 years. So when Stefan restructures it and pushes out retirement to 70 and intersperses work with 1 year sabbaticals — a light bulb went off.

Inserting 1 Year Sabbaticals

What I really want out of an extended adventure is the chance to #PUSHPAUSE to spend some time dedicated to personal growth without the distraction of work / routine. Learn some new things, hone some existing skills, pursue some projects that have been sitting on a self, and open up room for new creativity. With that in mind I started realizing if I did volunteering / work exchanges — through Workaway and finding online remote work + starting businesses I could try to stretch the $ I’ve saved to make a year actually possible.

So as my coach hammer’s into me every month — let’s get specific:


  • How do I reach a level of surfing of consistently being able to tackle more difficult waves (barrels, and turns)?
  • How do I learn to cook more healthy meals?
  • How do I learn more salsa dancing?


  • What are some passive income opportunities I can develop on the side to give myself more freedom in choosing what I do after 1 year sabbatical?
  • How do I turn Sales Ops experience into a course / remote consulting engagements?
  • What can be done around rental electric scooters in Surf towns?
  • What would a rental vacation property look like?
  • What are some areas that spark my interest on where I can take my career next? Governance Transparency, enabling marginal groups with technology, reducing single use consumption → cyclical business ecosystems?


  • How do I learn conversational Spanish and Vietnamese?
  • What are ways I can contribute Time Volunteering vs just Money to causes around Ocean Environment and access to education opportunities?
  • How can I help others build mechanism’s / tools to live happier lives?
  • How do I attract the passionate, adventurous, ambitious partner I want?


Ok, now how do I make the jump? Easier said then done lol there’s the tactical/logistical issues of bank accounts, work visa, etc. but there’s 3 mental exercises I always have to remind myself to do to help me conquer the fear.

1. What’s the worst that can happen / worst case scenario?

This is removing the fear of the unknowns, or at least being ok with ways of mitigating it. There’s things like travel insurance in case something unexpected happens, yet this is more like:

  • I use up my travel fund faster then expected → have buffer points/$ to book a flight home
  • I can’t find a job afterwards towards my career, my savings/investments get wiped out → Move back to Canada crash with family, friends, do odd jobs / take a entry level ops admin work. Start again.

You might be stuck with me… again…

Once you go through worst case scenarios and have thoughts on how to mitigate, the risks don’t seem as big. This leads to the question then: What’s the best case scenarios/upside to the decision I am making?

2. How to Setup Accountability / Breakdown to Smaller Pieces?

Well this post is step one, but publicly sharing, having others hold you accountable is a strong motivator to keep you focused. Writing your resignation letter and putting in an envelope dated x — Just don’t tell my work yet ;)

I also find that breaking things down into Quarterly chunks helps me a lot.

What would 1 Year Sabbatical look like Q by Q? What are things I need to do to prepare / research by? Bank accounts, taxes, insurance, lease swap, selling furniture, storage, etc.

3. Remember — Nothing is Permanent and you can always get back to now

This is one that I always forget yet is probably the simplest. No decision is permanent, if I want to change 3 months in because an opportunity comes up, or I am not getting what I want out of the experience, I fall deeply in love and decide I want to run a surf hotel, I can. That and where I am RIGHT NOW, I can always get back to here because I already know what I had to do to get here.

What’s Next?

Tentatively aiming for October to begin the adventure after Burning Man (finally decided to go before I leave Cali). My work won’t know until later as I work with them on a transition plan for my role, so please don’t post on my LinkedIn hey how’s your trip :P

Star Alliance — Round the World — Flight Planner

Rough Plan

Now — Sept (USA Wrap Up)

1 Year Sabbatical

  • 5 Months (South America: Costa Rica, Columbia, Peru, Chile)
  • 1 Months (OZ + NZ )
  • 4 .5 Months (SE Asia — Bali, Philippines, Vietnam, Layover Singapore)
  • 1.5 Months (South Africa, Stockholm — Job Hunt, Portugal — Check out land)

Think my next post I’ll share more around what I am doing to prepare, ie. intricacies of bank accounts without residency, investment accounts, doing a lease swap, booking around the world award flights on points, etc.

Until then let me know how you deal with making big decisions / overcoming fear? Keep me accountable. Know any people that need help scaling up their sales teams? and if you want to see me somewhere along the way / have a couch to crash let’s make it happen :)




Brian Huy Mac

Everywhere you go, there you are