run businesses

I now officially run businesses, two of them, and am involved in brand standards and procurement for yet a third. But I still manage to do whatever I want most of the time, work from wherever I want, and wake up whenever I want. It’s pretty much exactly what I had hoped for when I started on this journey almost 6 years ago in late 2010.

I’m not going to bullshit you and pretend I run a four hour work week. I still work a lot (A LOT) but it’s on my schedule, and my terms, with the people I want to engage with and no one else. That’s the stuff that matters to me. That is my Republic of Freedom, right there.

So how do I manage it all?

My entrepreneurial life can be split into two realities: stable and fluid.

In the half-decade since starting my first business, I’ve either been:

  1. based in one place which I used as a jumping off point for travel (stable) or
  2. living out of a suitcase, on ships, in people’s guest rooms, and in hotels (fluid)

How I work depends on whether I’m in stable or fluid mode at the time. But the end game is the same – I make my living through selling my expertise and my only obligation is to make that work, whatever my circumstances.

All of my work strategies have been borne out of necessity. Because there is no plan B. There will never be a plan B.

All of my work strategies have been borne out of necessity. Because there is no plan B. There will never be a plan B. Click To Tweet

And you know what? It all works pretty damn good.

So when do I work if I’m always all over the place?


I set dedicated daily hours during my peak mental clarity phases. Usually that means I work in the morning from about 7-11am and then if I have a lot on my plate, from about 3-5pm. That’s the structure I stick to, but if someone invites me out to do something fun and I don’t have pressing projects, I opt for fun, always.

When I’m in a stable phase, I have to harness different parts of me. I have to work harder to overcome resistance and distractions to just DO THE WORK and ship when I decide it’s ready. Sometimes work is easy, and sometimes work is really hard. Sometimes I’d rather stick hot pokers in my eyes than write a batch of tweets, but I fucking do it anyway because I’m dedicated to an ideal that’s much bigger than me.


I literally work when the opportunity arises. In the edges of the day. In the passenger seat tethered to the internet via my iPhone on a local SIM card. Taking client calls at the ski hill lodge where they have free wifi before hitting the slopes.

This is the reality of it and while some of you might cringe at the idea of writing blog posts or course content while sitting in the passenger seat on a road trip or on an 8 hour plane journey when everyone else is sleeping, I love it. I often get most inspired when IN the journey, and I want to capture all that stuff as it comes to me, otherwise the best is lost.

That doesn’t mean I work ALL the time when I’m free – it means I work whenever I can fit it in that my brain is also good to go. Uninterrupted stretches of time don’t always go hand in hand with creative flow. And yes, consistency is harder to maintain when I’m living in one of these phases but that’s why I have an assistant and why I use a lot of digital tools to keep me organized.

That said, my work is an extension of myself and most of the time it’s not hard to prioritize because I love it. And prioritization is the key word here: if I know I have little time, I just look in Google Keep and make sure I tackle the highest priority items so I never feel like I’m behind or have dropped the ball.

My (not so) secret work arsenal

Here are five apps I use to manage my businesses no matter what mode, country, or mindset I happen to be in:

Google Keep to gather all of my to-do’s in one place

Google Keep….free, dynamic, cloud based so I can access from my phone or from someone else computer. I love it! I love that I can colour code things and set reminders, and that it integrates with Google Calendar seamlessly. Yes, Google technologies have sucked me in and held on tight. What can I say? They make my life super easy.

Evernote to stockpile resources and write drafts of blog posts

I don’t know what I’d do without Evernote. I write all of my blog posts in Evernote and occasionally share things with my virtual assistant (via the handy Share feature!) so she can proofread or comment on things. I also save a lot of useful stuff I find on the internet in there for future reference. You can save web pages or portions thereof, and tag them with keywords to make it easy to search for them later within Evernote. Seriously, Evernote is one of those resources that’s worth taking the time to get familiar with.

Dropbox to upload files I need to send to people or share with my readers

I use Dropbox to store things like PDF’s I make for my subscribers or resources to send to clients. I love Dropbox because I can access it even if I don’t have my own laptop nearby.

Latergramme to schedule stuff I want to post on Instagram

I know it kinda defeats the “insta” in Instagram but I’ve been using Instagram more and more to share things like blog posts and throwback photos and, quite frankly, I’m hardly ever in the same time zone as most of my followers so Latergramme comes in handy. Again, consistency is what I’m going for so a little scheduling goes a long way.

Hootsuite to schedule tweets leading people back to my writing in order to broaden my audience

I use Hootsuite but you could just as easily use Buffer or the paid app Edgar for social media scheduling. I mostly use it to post to Twitter and a little bit to my FB Business page, but I have it linked to all of my social media accounts so that my assistant can share my work around liberally. The more eyes on your stuff, the more chance you’ll have to make an impact. That said, I do make sure to interact on Twitter, Linkedin, and anywhere else people have responded to my work because it’s lame to just post from Hootsuite and never treat people like humans on the other end. No one wants to be spammed with blog post links!

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