I recently applied for a visitors visa to Canada (officially known as a ‘Temporary Residents Visa’) because my best friend is getting married in July. I went to Canada about 3 years ago for his brother’s wedding - around the same time of year - and it was nice. I have been looking forward to the trip.

Granted, I had my suspicions that my application was weaker than it could be - for a number of reasons.

I am a bootstrapper. A few months ago, I started doing freelance web development to pay the bills. The issue with that is the cash flow fluctuates significantly. So when a good month happens, I have to put aside for slower months. 

Needless to say, I couldn’t provide a ‘job letter’ or show any ‘proof of employment’ to a Jamaican company that requires that I live in Jamaica - because no such thing exists. The best I can do is show company registration documentation, and bank account statements in all my bank accounts (locally, and US-based). Also, the application process has collided with a “slower period” - so the bank statements are not flattering, to say the least.

I don’t own where I live, I rent. 

I purposely chose not to use my parents as financial support, because…well…I am almost 30 and have 2 kids (with 1 on the way). Plus…I earn my own living (kinda), damnit!

Before deciding to go down this road, I read ENDLESS stories and blog posts about others that have trod a similar path. I debated doing something where I raise money, or bootstrap. I hated the idea of losing control and I seem to have an affinity to doing things the hard way (not that raising money isn’t the hard way).

One of the things I didn’t quite realize is that even though you are bootstrapping, life doesn’t stop. You still need to interact with institutions that don’t understand the concept of a bootstrapper or even the startup life or even freelancing.

So let this be another data point you should consider when you think about bootstrapping. I always thought, “nah…that will never happen to me”. Seems it’s more the rule than the exception.

Now, it seems, I will be missing my best friend’s wedding in July. 

I read about rock-bottom, but never knew what it felt like. I know you might scoff “Pfftt…I used to live in my car”, but compared to what I am accustomed to, these last few months have been pretty damn hard and this almost feels like the nail in the coffin.

I am a pretty private guy, but I didn’t know what else to do other than let it all out.

The worst part about this all, is that I can’t see myself doing anything else - no matter how tempting it may be.

In other news, I am working on another product that I hope to launch in the coming days/week. If you are a freelancer, and want to find new business leads easier, follow me on Twitter so you can know when I launch that.

Can’t stop, won’t stop.

This is the life I chose, or better yet, the life that chose me.