This week, I had a bit of an identity crisis.

I’ve been traveling for the last 5 months, and was laid off from my remote tech job 2 months into my travels.

But now I’m wondering if it’s a mistake to not find another job…

Hence why this email send is a few days later than usual.

Here’s what happened (if you’re curious about the life of an influencer digital nomad)

I’ve been to these countries the last few months:

• Australia

• Vietnam

• Taiwan

• Thailand

• Japan

I’ve made amazing memories, but when you’re a business owner (with no proper systems set up), you’re never really “on vacation.”

I’m very privileged to be able to travel and work at the same time - some people would say that’s the dream.

And it was for me, for a while.

But then I started looking at my monthly expenses.

My fiscal year ended, so I had to sort out my accounting and bookkeeping (which I did all wrong).

I got a sponsor opportunity for Universal Studios Japan, and spent Halloween filming (but also wanted to enjoy the moment…so none of the footage is good).

I started thinking about my future.

My friends’ companies all have so many benefits -

Including retirement plan matching (not sure what it’s called because I’ve never had it).

And they didn’t have to spend months chasing down their insurance company,

Just to get them to stop charging so much.

They didn’t have to feel stuck overseas,

Unable to call the CRA (Canada Revenue Agency) about the overdue late fees because they weren’t home to receive mail.

Maybe living the startup/entrepreneur life was fun for me in my early 20s,

When I had years to spend exploring my interests.

But now, I feel worried about my future.

Because if I can’t make this work, my whole future is at stake.

So I took my own advice

I implemented the frameworks I teach in my life tracking course.

It feels like ages ago when I created that course (while traveling in Australia).

But I’d feel like a hypocrite if I wasn’t “perfect” or “productive” like everyone thinks I am.

So I went back to the basics:

1. Asking myself why 5 times

2. Re-aligning with my goals and values

3. Creating a list of actions to do today, tomorrow, and later

Ask why 5 times

This helped me get to the root cause of my issue.

When I asked myself why I was feeling overwhelmed and wanting to “quit and get a regular job”…

The answer was lack of financial security.

But I dug deeper and asked why again, multiple times.

I realized everything stemmed from a lack of self-confidence.

I was telling myself I couldn’t do it, entrepreneurship is too hard.

I was telling myself I was a failure.

I told myself “it’s easier to get a real job” which made me put less energy into my own business.

So how you talk to yourself matters.

I’m going to try telling myself I can make my business successful long-term, and see what happens.

Re-aligning with my goals and values

One of my values is growth - putting myself through challenging experiences to learn from them.

(That’s why I run marathons and why I went on the most treacherous hike of my life in Japan.)

I realized that if I just got a regular job,

I wouldn’t be living in alignment with my values.

And my goal - my North Star Metric for my life -

Is to positively impact as many people as I can.

And I have a better chance of achieving that with my own business.

Things to do today, tomorrow, later

Today

• Seek support from a community

Tomorrow

• Catch up on things that give me energy (editing fun videos)

Later

• Figure out accounting stuff :(

If you’ve ever struggled with something similar as an entrepreneur (burnout, imposter syndrome, etc.) - I’d love to hear from you!

Vote in the poll below or reply to this email ❤️ 

Til next time,

Jennifer