Pushing Pause — Planning the Jump


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.


  • 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.

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 ;)

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

Rough Plan

Now — Sept (USA Wrap Up)

  • 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)



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