When Safe Isn't Enough: Navigating Risk, Anxiety, and Career Pivots - Andrew Woodbury

"Risk is what's left over after you've thought of everything. You can plan out the perfect business idea, and after that, there is still an element of risk that exists. There is no riskless starting of anything; you won't find out what it is until you start."

In this special episode of our entrepreneur series, the tables are turned as Leo interviews his co-host and business partner, Andrew Woodbury. Andrew reflects on his journey from an anxious humanities graduate to managing TEFL programs abroad, leaving the post-secondary system, and learning to navigate the reality of business risk.

Andrew is an educator, business owner, and co-founder of Learn Your English and ImPact Canada. An advocate for experiential career shifts, he breaks down the myth of "riskless" starting, managing double-ended anxiety, and how he is using ImPact Canada to provide newcomer entrepreneurs with capital, safety nets, and side-door access to build thriving businesses.

In this episode, we discuss:

How an introverted history graduate accidentally fell in love with teaching after taking a leap to Costa Rica.

Why tricking yourself into a temporary 6-month commitment can be the exact push needed to cross international borders.

Navigating the sharp contrast between an introverted personal identity and an energetic "Mick Jagger" teaching persona.

Floating in Oaxaca, Mexico, and realizing that 2 weeks of annual vacation in a traditional 9-to-5 wasn't going to cut it anymore.

Choosing to leave a university program before the ship sank, and weathering the panic of COVID-19 without a safety net.

Dealing with the unique fear of stepping into the unknown vs. the stagnant anxiety of staying in a job you've outgrown.

Why newcomer qualifications are routinely ignored in Canada and how to replace patronizing resume workshops with real financial access.

Creating a community venture fund to give newcomer entrepreneurs the side-door access and safety net usually reserved for legacy citizens.