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We just returned from a one-week vacation in The Azores, a nine-island Portuguese archipelago known for its centuries-old buildings, volcanic topography, breathtaking vistas, and the fact that nobody can seem to agree on whether it’s called “The Azores” or just “Azores.”  

As is our habit, my wife Linda and I eschew (SAT word!) tours and guided trips. Instead, we prefer to plan things ourselves and make our way solo.

Granted, this approach is not for everyone. Invariably, when you do it yourself, there are challenges and hiccups along the way. Examples…

• The Azorean streets are cobblestone, steep, and medieval-era narrow. Trying to parallel park an unfamiliar car with a manual transmission without rolling into the vehicle behind you requires a precise touch, a lot of luck and, often, a wardrobe change.
   
• On our last day there, we made plans to stop for a quick lunch in a little town before heading to the airport. Unbeknownst to us, it was “Portugal Day,” meaning that half the restaurants were closed and the other half were filled to capacity with celebrants.
   
• The restroom symbols indicating “men” and “women” are unfamiliar and often confusing, sometimes leading to disastrous results (again, please accept my apologies, madam).

But… there is also a wonderful flip side to traveling this way. It’s unscripted and off the beaten path, something that always leads to unexpected experiences and interactions:

• Accidentally stumbling upon a kids’ football (soccer) tournament, where we drank beer while watching alongside a very animated group of parents.
   
• Arriving late for our dinner reservation because the road was temporarily blocked by a 30-person, multi-generational marching band coming down the street.
   
• Spending time with the host of our rented apartment who met us at the airport, cooked us dinner the night we arrived, and answered all our questions (I regret not thinking to ask about the restroom signs).

So, which is better … traveling as part of a tour or doing it on your own?

Of course, the answer depends on what you prefer. And while we favor flying solo, I certainly see the appeal of having somebody else do the planning and smooth the bumps along the way.

Interestingly, these types of tradeoffs are very reminiscent of the differences between having a job and working as a solo professional.

On a day-to-day basis, a job is more predictable, both in terms of the work and the money. Working for yourself, on the other hand, tends to have higher highs, lower lows, and some occasional crazy.

Here, too, there’s no right answer – there are pluses and minuses on both sides. But if you are thinking of working for yourself, I can share a little of my own experience…

On the “challenging” side:

• No sick days, no paid vacation, no annual salary bumps. Over 25 years, I’ve been fortunate to have never had a serious health or personal issue interfere with my work. But if I had, there’s nobody here saying, “take all the time you need.” The money stops when you stop.
   
• You need clients. Amazingly, it never occurred to me before leaving my last job that nothing happens until somebody hires you. The hard part isn’t doing the work – it’s getting the work. And that reality never goes away.
   
• It can feel isolating. I happen to like spending hours alone in my office and doing everything from client work to taking out the trash. And yes, there are colleagues, partners, and clients with whom you interact. But unless you are trying to build something bigger than yourself, it’s not a team sport. Think about the environment you prefer.

But, along with those negative-ish things, there are some great aspects to working solo – things you don’t often get in a job:

• You’ll feel your own power. I never really knew what I was especially good at until I stepped away from all the noise and inertia that comes with being a small part of a big machine.
  
  Out here, not a single thing happens until you make it happen. When you start getting some traction, recognition, and success, it’s a pretty nice feeling knowing you did it all.
   
• You’ll make your own rules. Work when and where you want. Price and package your services however you like. Choose your vendors, choose your clients, choose your partners. Whatever you want to do, nobody tells you otherwise.
  
  And that guy who always insists on “playing devil’s advocate” in every meeting? He’s not here. It’s your company; do whatever you like.
   
• You’ll never wonder, “Maybe I should have gone for it?”
  
  There are no guarantees, of course. I’ve known plenty of people who either couldn’t make it work or simply realized they preferred having a job.
  
  But win or lose, you’ll be in the game, at least for a little while. So however it goes, you can check that box and never regret what might have been.

Here’s the bottom line.

Like choosing how to travel, different people prefer different working conditions.

But if you’re okay with the uncertainty and all that goes with it, I’ve found the upside – in both cases – to outweigh the risks.

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