When is the Right Time to Scale?

Somebody once told me, “there’s never a perfect time to have a baby.” I took that bit of wisdom and stuck it in my back pocket for a time far in the future.

And the time has finally arrived. No, I’m not having a baby.

For a long time I’ve been wanting to scale what I do, but so much of what I do seemed to not be scalable. After all, I’m a writer and content marketer. My bread and butter are the words I put on the page.

I had experimented with hiring VAs and freelancers in the past to help with things I’m not so good at, but it never seemed to work out. Now, I think I’ve finally figured out what I was doing wrong.

First, there’s never a perfect time to scale.

We’ll always want just a little more money in the bank, just a bit more cashflow. We’ll want our processes figured out a bit more and our project management system set up flawlessly. We’ll want just one more client or to wait until we finish that big looming project. The timing is just never right.

Second, we give up too quickly. We hire one freelancer that doesn’t work out, one VA that doesn’t seem to take initiative. We fail to give proper instructions and eventually we decide that our new hire isn’t worth what we’re paying them. So we let them go, and conclude that there’s just no good help out there.

But both of these are fallacies.

Of course the timing is never perfect. You have a life! Lives aren’t convenient. They are messy and chaotic and filled with surprises, both good and bad.

And of course there is good help out there. But we can’t conclude our search after two or three people over a few years. It takes way more trying than that, for sure.

And the kicker is this: scaling is a job. You have to train the people and set up the systems and take the initiative. In the beginning those are things you simply cannot phone in.


It’s Probably Not What You Think

When somebody slights you, puts you down, or doesn’t include you, it’s probably not what you think.

In all reality, it’s probably a coincidence. Or at the very most, a reaction based on frustration, distraction, or some other impairment.

When you feel yourself reacting to somebody’s slights against you, pause for a moment and think about what else could be going on.

Most people are hopelessly wrapped up in their own lives. So, whatever negative emotions they carelessly lob in your direction, it’s probably nothing personal.


If you break the chain, repair the chain.

One of the goals for this blog has been to publish every single day. Many people set goals like this whether they’re tying to quit smoking, add an exercise routine to their weekly schedule, or what have you. And, like many who’ve come before me, I’ve delivered on my daily writing, without exception, until now.

After 48 daily articles, I broke the chain.

Perhaps it was the culmination of events at the end of the year, the oncoming holiday week, or the conclusion of several stressful events. Whatever it was, something stopped me from putting words on the page.

So I took a couple of days off. And in all seriousness, I considered stopping the daily writing altogether. For all my talk about commitment, it’s funny to flip my opinion 180° in the matter of a day or two.

I think the reason the lethargy sets in, once a chain is broken, is that we have a weird belief about chains. Unlike literal chains, we think that once a habit streak is broken, we must start over completely. However, in the real world you don’t throw a chain out when it’s broken, you simply repair it.

So today I’m setting out to write the two missing articles, backdate them, and start tomorrow as if the break never happened.

And I think there’s a powerful lesson in this for everybody struggling with a commitment.

Which is to say, if you break your chain, don’t replace it. Repair it.


What it takes to be successful.

What does it take to be successful?

Perhaps it takes unrelenting daily habits. Perhaps it takes a massive amount of funding. Perhaps it takes the right upbringing or the right group of friends.

Certainly all of these can contribute to some form of success.

And yet there are countless people without any of them who’ve achieved incredible feats.

That’s because success doesn’t follow many rules. In fact, there are only two rules that I can think of:

  1. Defining what success means
  2. Getting there by any means necessary


When we commit to something the idea is that we follow through no matter what. No matter if we have access to our typical tools or not.

The point isn’t to do the thing in a a specific way every time. The point is to follow through.

If you’ve committed to a project deadline and the internet goes down, borrow somebody’s hotspot or find a nearby cafe.

If you’re aiming to paint a new portrait every week but you’re traveling, there are art supply stores in nearly every town, not to mention tutorials online for making your own paint.

This post didn’t originally appear on my blog, because I didn’t have access to it at the time. But here we are.

It doesn’t matter what’s going on, just get it done.


3 Essential Strategies For Creating Content in Unfamiliar Territory

Today, my friend Jean asked me a fundamental question about content marketing. How do we create meaningful content for people or industries when we lack the proper domain knowledge?

For example, if you’ve been hired to write for a technology startup, but only have passing knowledge of the tech at hand, how is possible to create something worth reading, listening to, or watching for the prospective audience; an audience who, more than likely, possess deep troves of industry knowledge that surpasses your wildest imagination?

First, recognize that this is normal. Great writers and content producers aren’t always domain experts, nor are domain experts often great at producing incredible content.

Second, while the luckiest position to be in is that of the domain expert when it comes to creating content, domain expertise also has its downsides.

For example, I’ve been a “coworking expert” for a few years now. But that expertise is based on a narrow experience and scope of the industry. Which means I’m liable to create content based on a limited supply of information; material that could be, at best, terribly biased or, at worst, disastrously foolish. While domain expertise makes content creation a fair bit easier, it also tends to limit your exploration of new ideas and media.

So, what strategies do non-domain-experts use to generate great content when they have no clue what they’re talking about? There are three.


Don’t underestimate the awesome power of conversation. Interviews with people more “in” than you can generate amazing insights. What’s more, because you don’t have an insiders perspective (at least not yet) you can see things differently. You’ll latch onto concepts that others miss because you don’t have their same tunnel vision.

Interviews don’t need to be with keynote speakers at the annual industry conference. They need to be with somebody who has something interesting to say, and more knowledge about the industry than you.

You can record these interviews as a podcast or for useful reference material for an article.

You can conduct these interviews with customers, suppliers, or even employees within your organization. All of them have something interesting to say. Your job is to take the raw data and make it sing.


One of the best ways to get an all-access pass to expert-level domain knowledge is to become an insider. Join all the Facebook groups. Go to all the conferences. Watch all the Youtube videos. Give yourself a crash course on the subject, then go more in-depth.

Writing about ecommerce? Start your own online store as a test.

Vlogging about wine? Take a job at a local wine bar, no matter how low the position.

Podcasting about psychology? Start recording conversations with your friends majoring in the subject at university.


This is the good ol’ fashioned tactic I like to call studying. However, I think about studying differently.

I like to learn with what I call passive intent.

Passive in the sense that I’m not aiming to get anything specific out of the material.

Intent in the sense that I do intend to get something out of the material with every pass through it.

So gather all the podcasts, audiobooks, books, and blogs you can find on your topic. Keep them at the ready, so you have material you can start absorbing between projects, on your commute to work, or while on the can. If you lose your train of thought, don’t worry, that’s not the point. You can go back to review what you missed if you want, or you can keep going.

I’ve sometimes found myself missing near-on entire chapters of audiobooks because I was doing something else while listening.

This approach works because I don’t listen to or read books once. I’ve become an “expert” in various topics, not because I’ve listened to many different audiobooks or podcasts on the subject, but because I’ve listened to the same ones more than 20 times. You’d be surprised at the stuff that seeps in, even when you think you’re not paying attention, and you’ll be confounded when you hear a brilliant bit of insight that you somehow missed on the last listen-through.


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The Most Important Person In Your Business Is Not Who You Think It Is

In Season 1 Episode 4 of Hotel Hell, starring world-renowned chef and TV personality Gordon Ramsay, a self-interested building owner is in dire straights. His “luxury” hotel is a nightmare of tacky design, under resourced staff, and awful food.

Gordon asks a group of staff and the owner a simple question, “who is the most important person in this hotel?” Sheepishly, they all admit that the owner, Eddy, is regarded as the top dog. His opinion counts and what he says goes. So much so that the hotel’s restaurant had over 130 items on the menu, as inspirations from the brilliant Eddy and his friends, typically things they’d eaten elsewhere.

Gordon, flabbergasted, boldly pronounces, “The most important person in the hotel is the guest!”

Now, who didn’t see that coming from a mile away?

But he didn’t go far enough.

The point is that as business owners, it can be terribly tempting to thing about ourselves first. We get so caught up in our needs, wants, and dreams, that we become selfish. We become prima donnas. We forget that we’re there to serve our customers.

But even more, if we’re in the service business, as I am, we’re there for even more. We’re there to serve our customers’ customers. What needs, wants, and desires do they have? What jolts them awake at night in a flash of terror? What elegant solutions do they yearn for, in vain hope that their lives will become just a little bit easier?

The most important person in your business might be your customer. And it might even be your customer’s customer. But in the end, the most important entity in your business is that dream. The dream the person on the far end of your supply chain is hoping to realize. That dream needs you and me.

Don’t let it down.


The Key to Connection and a Feeling of Home for Digital Nomads

Digital nomads, while often portrayed as living the dream life, globetrotting and interacting with new cultures, have a strong tendency to feel disconnected and alone after awhile. Especially for solo travelers who’ve recently moved to a new place, the life can feel quite isolating at times. Your friends back home don’t get you. Your family doesn’t get you. It sometimes feels like the whole world doesn’t get you.

But of course, there’s a remedy for this isolation. The typical methodology is to connect with other nomads.

And there’s no shortage of tools to do so. There’s Nomad List. There are coworking spaces and coliving spaces.  There are parties and meetups. There are nomad cruises and nomad trains and nomad sailing trips. Clearly, as a nomad, there’s no shortage of ways to meet people living the same life as you.

But this type of connection comes with a significant downside. Nomads, of course, are nomadic. They are your friend one month, but gone the next.

For some, this might feel fine, at least at first. Certainly it’s a great thing to have a group of globally connected friends, who you might happen upon in the streets of Berlin one day. But it can, and does, grow tiresome after a while.

Luckily, there’s an alternative. A key to feeling connected to the place you’re in, to the culture and the people who live there.

And that key is language.

I’ve spent more than a year mostly traveling in the Balkan region, mostly spending time in Bulgaria. My girlfriend is Bulgarian. We come back to the same village every three months. We have an apartment here. We love it.

As expected, when I first moved here, I spent all my time with other nomads, expats, and travelers. It was great to have that connection. It still is.

But in the time I’ve been here, I’ve also learned a lot of Bulgarian. (Hard not to when dating a local.) And it’s opened up my life in more ways than I can count. I no longer feel like a stranger in a strange place. The small village of Bansko has become home. I’m happy to say I can walk into most conversations and have a general idea of what’s being said. I can hold my own when it comes to most basic conversations. I can translate for other nomads. I can order taxis for my friends and read the menus when there’s no English version. I feel a sense of satisfaction when locals are surprised at my effort (seriously, they’re super surprised). What’s more, because the languages are so similar, it’s fairly easy for me to get by in surrounding countries like Macedonia, Serbia, and Bosnia & Herzegovina with a handful of minor changes to wording and pronunciation.

Now, language learning isn’t the easiest thing in the world, and Bulgarian is not an easy language. Nor am I anywhere near fluent. But something changes in your brain when you begin learning to speak in somebody else’s mother tongue. Your brain changes. Things become automatic. You begin thinking in that other language, when possible.

I also know Spanish. I took courses in the language for four years. It’s safe to say my Spanish speaking ability is miles ahead of my Bulgarian. But because I’m so engrossed in the culture, day to day, I almost can’t think in Spanish. We have several coworking members from various parts of Spain right now and I can’t stop saying “Da” instead of “Sí.” It’s weird, but kind of cool.

Anyway, no, it hasn’t been easy to learn Bulgarian, but it hasn’t been terribly difficult either. I’m taking it in strides. I still have a lot more to learn. But knowing the little Bulgarian that I do gives me a sense of confidence and pride when I speak it. It makes me feel like more than a nomad, more than a tourist. It makes me feel connected to the place I’m in. And that is probably a big part of why this place feels like home.

So if you’re feeling a bit disconnected, traveling the world with your backpack and laptop, I suggest two things:

  • Pick a base; a place you love that you can call home on a regular basis.
  • Learn the language. A little bit at a time. And get the pronunciation right (it matters).

If you do this, not only will you feel more connected, you’ll become the person the nomads turn to when they need a taxi. And that feels pretty cool.


Special Snowflakes: On Uniqueness and Unity

The term snowflake has taken on a common place in our everyday vernacular of late. Its original meaning was to convey the idea that we are all unique, special, and exquisitely alone in our us-ness.

And of course, lately the term has come to mean something different entirely. It’s become a way to slander, to deride, and to discredit. Anybody who is seen as sensitive is called a special snowflake, purporting the notion that somehow that person’s dissent from the norm is a form of weakness. After all, snowflakes are brittle.

As happens with most ideological or political arguments, we’ve ended up with two sides, two polar opposites battling for ultimate victory.

And of course, they are both wrong.

This is a snowflake:

It is undeniably unique, just like every human on the planet. Even identical twins are not truly one and the same. And because this snowflake is unique, it will fall through the air in a slightly different way than the other snowflakes around it. A wider edge might give it more surface area, so it catches the wind and flies further than the other snowflakes which crystalized around it at the same time. So yes, snowflakes and people are unique.

And this is a snowstorm:

Do you notice anything interesting about this snowstorm?

In this picture alone, there is not one snowflake, but hundreds of thousands of them. Which means a snapshot of the entire storm, at any given moment, would be made up of billions of snowflakes, maybe more!

But the storm, the grouping of snowflakes, follows the laws of physics. The group has the same general direction. While each snowflake is unique, none of them will suddenly fly off into space or decide to become a rock in order to get to the ground faster. After all, they are snowflakes. And the purpose of a snowflake is to dance through the air, in its own unique way, but eventually fall to the ground so that we all get to enjoy the beauty of winter.

I don’t want this metaphor to get out of hand, so let’s get back to reality.

Every human on this planet is wonderfully unique. I love that. It means we all have different gifts to give which can make humanity move forward.

But it’s our shared humanity which is important, far more than any one individual. It’s the coming together for a better world, and someday perhaps, a better universe, that makes our unique gifts so special because that means we have many ways to get there.

So, far from decrying the special snowflakes out there, I say we celebrate them. Because we are all special snowflakes. The grizzled marine veteran and the liberal arts student are both special, but obviously different.

And instead of using our special us-ness to divide, I believe we ought to be like the winter storm: filled with an infinite number of gifted individuals, all working toward one common goal.

So before the next time you accusingly call somebody a snowflake, take a long look in the mirror, because you may as well be telling it to yourself.

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It’s Okay If Your Career Is Winding, They All Are

You might experience regret. Specifically if where you are in your life now isn’t where you’d hoped you’d be several years ago. When we’re young we make bold plans based on our dreams and passions, but inevitably we abandon them for more practical pursuits.

That’s okay.

Where you’re at now isn’t where you’ll be in a year. And it’s not even close to where you’ll be in five.

That’s because all careers are nebulous, winding their ways along different paths, reacting to the flows of life and the terrain of the market.

Actually, if you feel like you’re on the wrong path, that’s good. It shows that you still care. And there’s still a possibility for change. The discontent you feel is your north star, your compass toward a better calling.

Follow it.

It might take you six months or ten years to become frustrated enough to quit your current gig to do something new, something closer to your heart. And that might feel far too slow for you. But be patient. Things come in their own time. Let the frustration build up until it becomes unbearable. Then make your move.

My own career is lightyears away from where I thought it would go ten years ago. But I no longer want what I wanted ten years ago. Sure, some of what I desired remains, but it’s changed. It’s evolved.

And of course, it’s still evolving. And it always will evolve. Contentment in life is a myth. As soon as you’re content, you’re dead.

So please, no matter where you’re at now, no matter where you want to be, understand that your discontentment is good. Great, even. Feel it. Cherish it. Let it drive you at night and on weekends to experiment with other paths. Let it consume your soul, and your bank account. Build it slowly, in the dark, without any credit, with only the joy of pursuit guiding you.

Eventually, perhaps soon, you’ll find yourself in a better place. A place that you’ll look back from and wonder how it was you got there.

All careers are winding. Not only is that fine, it’s the best thing you could hope for. Everything else is boring. Everything else is death.