Four Lessons Learned After Six Weeks Blogging Out of a Suitcase

You never know how to do something until you do it.

You can have an idea, plans, prep and previous experience, but everything in this world is unique unto itself. You can’t know exactly what something is like, how something should best be done, until you have the experience yourself.

Traveling entrepreneur Nick Barron, in a white t-shirt, smiles at the camera.

This photo was taken my first day in Maine. Six weeks later, I’ve learned a lot during my travels.

When I set out to travel and tell the stories of entrepreneurs I meet, I figured I knew what to expect and what to do. I’ve traveled. I’ve networked before with complete strangers. I can write, and have been blogging for years.

And, true, I didn’t come into this a complete novice, but there have been many things I’ve learned over the past six weeks about traveling, blogging and being a faux journalist such as I am.

The lessons learned really break down into two categories: travel and blogging.

Six-Week Lessons Learned

1) The most affordable travel is the travel in which you plan and research your trip. After months of fare alert emails, reading travel blogs and researching travel planning strategies, it’s clear to me you need to plan at least two months in advance in order to not pay high prices for your trip.

You also need plenty of time to research travel options. There are often multiple ways to get from one place to another. Sometimes transportation options have special deals or benefits that aren’t readily available, requiring you to do a little digging. And of course, if there’s going to be a temporary deal or a sale, you’ll likely need to give yourself time to benefit from it because the chances of your trip being discounted the day you want to buy is slim.

When planning for Montreal I looked into every conceivable way to get here from Boston, including ride sharing. In the end I realized Greyhound was cheap if I booked in advance, much cheaper than airfare, and actually wouldn’t take much longer than the cheapest flight I could find. Plus I noticed the route would take me through New Hampshire and Vermont in October, two states known for gorgeous fall colors, and two states in which I had not yet been.

2) Plan nothing the first couple of days in a new place. This really applies to my business, as I’ve made the mistake twice now (Maine and Montreal) of booking client calls on the first day or two after arriving in a new location. Invariably this turns into a significant personal challenge.

When you get somewhere new, you need time to get settled, especially if you’re planning to be there at least a month at a time. Getting settled can include everything from unpacking to buying some groceries to walking your neighborhood so you have a feel for where things are located. And getting settled always takes longer than you think it will.

Plus, the last thing you want to do when in a place you’ve never been is stay locked down somewhere working.

3) One month is not enough time in one place. At least not when you do what I’m trying to do, tell the stories of local entrepreneurs.

When first planning my time in Portland, Maine, I did research, contacted some folks and, Portland being a smaller city, figured a month would be plenty of time. Except once people in town knew I was there, I would get one to four emails a day the first couple of weeks from local entrepreneurs pitching me their businesses. I didn’t have enough time to meet everyone. Plus, as I met more people I was told about additional folks I should meet.

Especially since my client work is how I make a living, I can’t devote all my time to the pursuit of this blog. And, of course, I want time to explore and be a tourist.

This is why I’m planning at least a month in Montreal that doesn’t have a set end date. Not only is a month not enough time to get a good feel for a city’s entrepreneurial community, I need buffer time for people I discover during my time here. At least a month and a half should give me this buffer time, allow me to manage my client workload, meet a good number of Montreal entrepreneurs, and have a little time to explore the city and its surrounding area.

4) Get better at responding to emails and scheduling interviews. I’ve already decided my first hire, if ever I make it, will be a virtual assistant. I am absolutely horrible at managing email and my calendar.

There were some people in Portland I had every intention to meet, but because I took too long to get back to them or because I overbooked my calendar, I was unable to connect. This not only makes me feel pretty bad, it’s quite embarrassing. I’m a grown man with his own business, and I can’t handle email and calendar.

Considering the profit margins on my business are fairly slim right now, it will be a while till I get a virtual assistant, so I have to get better at email and calendar.

Of course, I’ve learned more than just these four things, but these four lessons are the most prominent.

It’s exciting and daunting to think about how much I’ll learn over the next six weeks. Stay tuned!