Making Serendipity Tactical: Is Randomness Part of Your Leadership Strategy?


Have you ever met a person, come across an idea, or found a resource that was precisely what you needed at exactly that moment in time?

These “happy accidents” bring us surprise and joy. But more than that, they are essential to moving us forward as leaders and learners.

Serendipity powers the social web. Tools and technologies are being created every day to increase our chances of “bumping into” something or someone we aren’t expecting, but greatly need.

I have built a network of fascinating and generous people online. These “random collisions with unusual suspects,” as my friend Saul Kaplan calls them, have led to great conversations, shared meals, meet-ups, conferences, events, and significant partnerships.

I would have never have experienced the richness of these individuals and partnerships, or even been invited into your lives, without serendipity. My place, position, and influence, on the web and off, is a result of something I did not plan. Something I did not aspire to. Something I did not even know I wanted.

Each year, as the number of thrilling and “happy” encounters happened, I began to wonder; how much of this was actually an accident?

I came to realize that much of this was due to my efforts to summon and shape serendipity, through a process I call “Tactical Serendipity.”

Tactical serendipity is the intersection between structure and spontaneity.

It is the ability, capacity, and frame of mind that enable a person to have more structure and spontaneity than he or she could have of either.

Tactical serendipity is the intersection between structure and spontaneity.

So if you are willing to take a few minutes a day in your consciously prepared, overly-planned, highly-articulated life to let serendipity do its magic, the following tactics will aid, accelerate, and amplify your chances of an encounter that will change your universe.

1) Put Some Randomness Into Your Routine.

Serendipity occurs when you go looking for it.

Not having an end game, not having a clear and defined outcome, is scary. How can I trust my learning, my work, and my heart to someone that I do not know?

Through the process of putting our guards up, protecting our identity, and summoning unnecessary barriers, we also condemn possibility, eliminate chance, and choose sameness and an uninspiring journey down the well-worn path.

Trust the Universe.

2) Get Out There.

Getting yourself out there, engaging the world with an open mind and exploring the unknown leads invariably to positive experiences, new connections and new opportunity and possibility. In particular, I’ve found that Twitter is a useful tool for accelerating the process of injecting random online experiences into my life and turning them into a source of offline fun, opportunity and possibility.

Share your genius with the world.

More openness to randomness = more connection = more sharing= more serendipity.

3) Connect.

One of the easiest ways to increase serendipity is to be a better connector. The easiest example of how to be a connector is to connect two people you know who you think can create special value together. The fun part is that those people you connect will credit you with the connection, and, if they’re smart, they’ll come back to you with opportunities for you!

Use your social media. Say hello to a stranger. Write your favorite author. Introduce people. Reach out. Offer your opinion.

More connecting = more serendipity.

I would have never have experienced the richness of these individuals and partnerships, or even been invited into your lives, without serendipity.

4) Tribe Hop.

We are most comfortable when we connect and spend time with people who share a common worldview, enjoy the same activities, and speak the same language. The most valuable tribe is a tribe of unusual suspects who can challenge your worldview, expose you to new ideas, and teach you something new.

Every interaction you have can shape your future if you take the time to learn and grow from it.

Shake up your perspective.

Read: My Twitter Engagement formula and 12 Habitudes for Social Media Success

5) Slow Down.

Hurry tramples watchfulness and thoughtfulness.

Have you ever walked to work or school instead of taking the train or the bus? During that brief moment in time you probably noticed things in your environment that you never had before, even though you take the same route every day.

Become a master at noticing.

The last time you got a haircut, did anyone notice that day? How did it feel when you got a compliment? How did it feel if no one said anything to you, no one noticed a difference?

Notice everything, especially taking note of the needs of others and responding with empathy and compassion. When you notice, you show others that they matter, and that corresponds to another connection, another chance to interact, and another opportunity for serendipity.

6) Invite Yourself.

Do not wait to be picked.

Politely, respectfully, and enthusiastically go to gatherings that you have absolutely no reason to attend other than you might learn something new, or meet somebody with a different perspective and experience. Make it a personal goal to attend gatherings where you do not know the people or subject matter. Better yet, go to gatherings that are designed to bring unusual suspects together and to enable random collisions.

Hurry tramples watchfulness and thoughtfulness.

7) Be the inviter.

Let people know where you will be.

If I am attending a public event, I put it out there so that if someone wants to connect with me, they easily can.


Collaborators are everywhere. You will find them in the gray areas between silos. Just look up from your current business model!

Seek out difference, and gather often across boundaries, disciplines, and sectors. Be open and be curious.

Make sure you seek out potential partners and “sandbox mates” from across every imaginable divide, and listen, really listen, to their stories. New ideas, perspectives, and the value creating opportunities are in the gray areas between unusual suspects.

9) Light a spark.

William Shakespeare said, “All things are ready if our minds be so.”

Open up your mind.

Change the conversation.

Issue a provocation.

Set the system into dynamic motion. If you ask the right question, you can stimulate a collective evolutionary potential, and a network will unfold. Light the spark that illuminates the best of what we know, and who we are.

10) Be a “Go-Giver.”

As my beautiful friend Bob Burg would suggest, one of the best ways to achieve your own awesome is to give, give, and give some more.

In a recent instance of serendipity, as I was writing this post, I was forwarded an email from Ari Kaplan, a networking and business development guru in the legal profession. Titled “Speaking of Serendipity,” it included a link to this free handbook, filled with excellent advice that dovetails neatly with mine.

Tactical serendipity is fully embracing the choice to be random, ready to accept the unexpected gifts from the random collisions you will encounter.

Take charge of your life. Take charge of your destiny. Make tactical serendipity a core part of your life.


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Image credit: egal / 123RF Stock Photo

My life path has always been about teaching and communication. My twenty years as an educator and my passionate pursuit of literacy and learning, gave me the healthy dose of courage and skills that have led me through a wonderful variety of experiences, including classroom and University teaching, instructional coaching, research, writing, publishing, corporate training, and starting my own business.

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