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I'm Tyler, and I created Riskology to be a community where introverts master their psychology and make a dent in their universe—little steps every day to build something great. Join 20,000+ others just like you on our (totally free) email newsletter and I'll send you our Leadership for Introverts test to build your skills.

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The Top 5 Introvert Leadership Challenges (and How to Beat Them)

Giving a singular voice to a group of people is hard work. Finding the little things that make people tick and motivating them toward a common goal is equally difficult. Those are big leadership challenges.

If you’re an introvert with big ideas, you must be up to the task. Your natural, introverted skills will propel you and your team forward, but you’ll also struggle with some fundamental challenges that keep you from stepping into a leadership role in the first place.

We’re always on the lookout for new research and ideas to help you capitalize on your natural strengths and succeed as an introverted leader.

Recently, we asked our readers, “What’s the #1 thing that holds you back from taking on more leadership roles?” From the hundreds of responses, we were able to categorize them into five primary roadblocks:

  1. Self-doubt. You’re unsure of your own leadership skills.
  2. Trouble being perceived as a leader. You may be confident, but others don’t see you as their leader.
  3. A lack of leadership skills. You know you don’t have the skills you need, and you’re not sure how to get them.
  4. Feeling inauthentic. You hesitate to lead because it doesn’t feel natural.
  5. No time / energy to lead. You’re already doing too much and you’re too tired to take on the responsibility.

If any of those answers sound familiar to you, then keep reading. We’ve assembled a complete guide to recognizing and fixing each of these roadblocks to leadership in yourself.

The world needs more introverted leaders, and you can become one of them—quietly affecting the lives of those around you for the better.


What the Heck Is an Introvert, Anyway?

What, exactly, is an introvert? The word has gained real popularity recently and people around the world seem to be coming out of the woodwork to declare, “That’s what I am! I’m an introvert!”

Google Trends for the Term "Introvert"

Here at Riskology, we consider ourselves introverts but, if we’re being totally honest, we don’t all agree on what that means and often struggle to explain it in elegant terms when someone asks us, “What do you mean, you’re an introvert?”

So, we set out to answer the question once and for all.

We dug into the history of personality science. We scoured the latest research and analyzed pop culture references. And we interviewed highly credentialed professionals in the field.

If we could break it down into three key findings, we’d say introverts:

  1. Have deep, rich inner-lives. It’s hard to overstate how “inside their own heads” introverts are.
  2. Prefer solitude to busy environments. Introverts are most at home… at home.
  3. Enjoy people, but prefer fewer, deep relationships. It’s all about quality over quantity.

But boiling down an entire personality type to just three bullet points can’t begin to explain the complex and fascinating traits of introverts.

What follows is a deep, multi-faceted look at what it means to be an introvert. Not just in the academic sense, but in the “How does this affect my daily life sense?”

So, where to start? How about at the beginning.


The 2015 Sabbatical: Why We Should All Take a Month Off

Tomorrow, December 1, officially begins the Riskology 2015 sabbatical. There won’t be any new articles appearing here for the month (with the exception of the annual review at the end of December we’ve all come to love).

Instead of writing, I’ll be spending time taking long walks, taking even longer notes, meeting with friends, and creating a plan to answer this question:

“What is going to make Riskology great in 2016?”

I started this practice last year and while it often sounds lazy to those who pride themselves on working harder no matter what, it’s been one of the most beneficial things I’ve added to my routine.

Here are the important things I do during my sabbatical that allow me to make huge strides in my life and business every year and, of course, a few ideas for how to implement a similar system if you don’t run your own business or can’t just disappear for a month like I do.


Tipping Points: How Introverts Spread Big Ideas


If you’ve spent any time listening to the politicians, CEOs, and gurus of the world, you’d be forgiven thinking that, to lead people or get them to listen to your big ideas you have to be an outgoing extrovert who spends every waking moment shaking hands and kissing babies. You have to get in front of everyone.

But is it true? No, it is not.

You don’t have to go on a world tour or try to evangelize to everyone you meet to be a leader and make a difference in people’s lives. Actually, you can make big things happen just by connecting with a few people. When you connect with the right people, you can share your idea, sell your product, get people to use your app—whatever it is you want to influence—without overwhelming yourself with work.

When you have a great idea and you communicate it to the right people in the right way, you can achieve a tipping point—the point where your idea will continue to spread without any effort from you—quickly and without burning yourself out.

If you’ve always thought you had to pretend to be an extrovert to get people to pay attention to your ideas, this could be a life-changing realization for you. In fact, introverts have a natural advantage when it comes to sharing powerful ideas. We’re hard-wired to build deeper connections with fewer people, so we naturally reserve our energy and focus it on the people who are most aligned with us.

In fact, if you want to get better at creating tipping points for your ideas, products, whatever, then you’d benefit from learning to be more like an introvert.

But how do you get started? How do tipping points really happen, and what do you need to do to make sure your ideas have the best shot at reaching one?

Let’s dig in.


Law of Equal Effort: How to Do Big Things Without Burning Out

A few weeks ago, I ran my eighth marathon. I’m hardly the world’s leading expert on running. I’ve never followed a formal training schedule, hired a coach, or joined a running club and I’m not fast—my PR is just 3:49:00—but I’ve always finished.

The training matters, but what gets me through a race as difficult as a marathon is an approach I take in my life that just happens to help my running, too.

I call it the Law of Equal Effort, and it’s incredibly simple: Regardless what life throws at you, you put in the same effort.

Following this theory, the progress you make over time can vary significantly but, in the end, you get to the same place and you feel a lot better when you’re done.

It’s an important approach when you’re taking on a long-term challenge and you don’t feel confident. And it’s an appealing approach because you’re in control. You don’t always get to decide when things will be hard or easy for you, but you do get to decide how you deal with the ups and downs when they come.

Here’s how you can put the Law of Equal Effort to work in your day-to-day life, as well as a few situations when you should take a different approach. We’ll apply it to three examples: running a marathon (naturally), starting a business, and building a relationship.


Your Tiniest Ideas Will Have the Biggest Impact

I spend a lot of time concocting lists of random ideas to make my life better. If I have a problem, I can immediately hatch a plan to fix it. Over the years, though, I’ve learned my “great ideas” cause more problems than they solve.

In the heat of the moment—stress building—I’ll come up with a complex scheme, and go off to implement it, not realizing the added complexity will eventually cause even bigger problems. Consequently, I’ve learned it’s when I have the restraint to follow my tiniest, most simple ideas that I benefit most.

The elegance of a tiny solution to a big problem is a thing of beauty. That’s why I love Southwest Airlines’s story of near failure turned massive success from the tiniest change.

It’s a testament to the power of tiny ideas, and it illustrates the rules for identifying, committing to, and following through on your best ones. How do you nurture a tiny idea into a great success? Like this. Continue…

How We Created an Introvert-Friendly Event: A Case Study of WDS

For five years, I’ve had the privilege to be behind, in front of, on top of, underneath and around the scene of The World Domination Summit. Our small team of founding members have watched the event blossom from just a seed of imagination to an event for over 3,000 people.

I’m constantly amazed by the people I’ve worked with. More though, I’m amazed by who shows up year after year: introverts. My inside joke is that I love planning WDS but I wouldn’t attend because I’m too introverted.

Really, though, I would attend WDS. It’s one of the only events I would go to—whether 100 people or 10,000. We’re far from perfect, but something we got right from the beginning, and have got right all along, is making an event where introverts—people like me (and, perhaps, you?)—feel at home.

I’m proud of that because many events do an extraordinarily poor job creating a comfortable environment for us. They assume we don’t want to go to events, or there’s nothing they can do for us. Both assumptions are, of course, wrong.

WDS is a haven for introverts and extroverts alike, and that’s not by accident. I sat down recently to think about decisions we’ve made over the years that have created that welcoming environment. There were a few key decisions and actions that helped cultivate it.

My goal sharing this today is twofold:

  1. I hope it equips others creating events—from dinner parties with friends to multi-day conferences serving thousands—with some tools to make their events better for the 50% of the world they may be underserving.
  2. I hope it helps introverts like me—who enjoy big events but are easily overwhelmed by them—pick better events to attend.


The System I Use to Write My Best Every Week

As an introvert, I sometimes struggle with communication. It’s hard to get my ideas out in a useful way in conversation. One place I excel, though, is writing. When I write, I can take the time I need to craft my message just the way I want it. Everything comes out polished because I have time to edit and really think about what I want to say.

But just because writing is my strength doesn’t mean I always do it well. A few months ago, I read my recent articles and thought to myself, “These need more work.” My ideas needed more thought and more attention before publishing.

I was constantly stressed. The second an article was done, it was time to start the next. It became normal to stay up too late to finish writing only to be disappointed in the results.

So, I cut my production in half and started publishing once each week instead of twice. That would fix the problem, right? It didn’t. It lowered my stress, but quality didn’t get any better.

I didn’t have a writing problem. I had a habit problem. My writing habit was broken. Instead of procrastinating twice each week, I just did it once. It was a welcome change, but not good enough. If I wanted my writing to  improve, I needed a system that would help me spend more time working on my writing instead of wasting it on something else.

So, I built that system and, for the last three months, it’s helped me drastically improve my writing by allowing time for my thoughts to get clearer, time to carefully edit and, my favorite part, add useful illustrations.

Below are the steps I followed to set up my writing system. If you’re an introvert like me, you might find it helps you take your strongest communication style to another level. Continue…

A Tribute to Scott Dinsmore

Twenty-four days ago my friend, Scott Dinsmore, passed away near the summit of Mt. Kilimanjaro—the same mountain I struggled on four years ago.

Scott was the larger-than-life founder of Live Your Legend, a community dedicated to helping people find and do the work they love. His accomplishments—and the lessons I’ve learned from his friendship for the five years I was blessed to have him in my life—are too many to list here.

In the days since his death, thousands have turned out to mourn and share their stories. [1]

I knew I would have to share mine, as well. Until today, though, I didn’t know how. Trying to eulogize someone like Scott would only make me look like a hack. I’ve tried (and failed) for weeks to find the words to do him justice. So, I’ll share just three stories from our too-short time together that will tell you a little about who he was to me.

When I think of these stories, they inspire me to be a better person. I hope you find them useful. [2] Continue…

Practical Ways to Find Creativity When You’re Feeling Uncreative

It was a tough day in the trenches at The Travel Hacking Cartel, a business I run with friends.

We’d launched a new feature and the support inbox was blowing up with requests to test it out. Just when I’d worked through the backlog of support tickets (yep, I still do the support tickets), one last message comes in from Nora, a longtime member:

Hi, I’m checking my credit card statement and it looks like I’m being billed twice every month.

Hmm, haven’t seen that one before. Sure enough, though, two accounts had somehow been created, and she’d paid twice for a long time.

Looking back, there are lots of ways to solve this problem but, in the moment, I was tired and uncreative. I couldn’t see an easy answer to the problem. So, I do what I do every time I feel burned out in the middle of the day; I head to the coffee shop. I order kombucha and hand over my credit card. The barista starts to pull the tap and, halfway though, it starts to fizz out. She moves to the second tap and tries again. Nothing. Kombucha’s gone.

The barista looks at me with a frown and apologizes. I’ve already paid, but there’s no kombucha and she can’t run refunds from her terminal. She thinks for a second and comes up with the perfect solution: “If you want to order something else, I’ll give you a gift certificate for a kombucha. Come back tomorrow and it’ll be ready for you.” I happily took the offer and was on my way.

When I sat down with my revised order and opened my laptop, I knew exactly how to respond to Nora:

Hey! You’re right. I’m so sorry about that. What if I take what you’ve paid so far and credit your account so you don’t have to pay again for a long time?

Nora was perfectly happy with that, and the problem was solved.

Neither of these scenarios are what you probably think of when you think of creativity.[1] No one wrote a song, drafted a book, painted a mural, or designed a product. But they were creative. They were unique solutions to a difficult problem.

Creativity is all around us but, for so many, it remains invisible—hidden in plain sight—because we’ve conditioned ourselves to look for it in only a few places. There are so many places you can draw new ideas from to improve your work if you look just a little harder.

When you have a problem to solve or need to create something new and keep coming up short, try these practical ideas for finding inspiration and upping your game. Continue…