When Flailing Becomes a Business Strategy

Emily Crookston
6 min readOct 20, 2020


Photo credit: By Maddog 229 from Pexels

Opportunities come in a variety of forms from a variety of sources. When we’re new to running a business, we know this. Or more accurately, we spend so much of our time flailing around like some kind of Tasmanian Devil that we somehow end up bumping into a variety of opportunities.

The flailing may not be intentional, but in the beginning, it’s exactly what we need to figure out how to build a successful business. Somewhere along the way, though, we end up with tunnel vision:

  • We buy into stories about the ONE secret to making millions…
  • We niche ourselves down into oblivion
  • We end up playing small when we once had such big dreams

During the past several months, I’ve had a taste of that early feeling of flailing around again. And I realized something important: I miss flailing around and chasing down opportunities.

On Failing and Flailing

Wait. What? Yeah, I know. It’s weird for me too.

When I quit my job as a philosophy professor and started The Pocket PhD four years ago, all I wanted was for someone to give me the syllabus and tell me how to get an A. In other words, I wanted to know the shortest, neatest, most efficient way to make money as a content marketer.

I listened intently to all the advice I could cram into my head:

  • Figure out who your ideal client is
  • Find your “why”
  • Write a business plan
  • Change the name of your business
  • Become a word factory cranking out content every waking moment

I tried to follow all of this advice, failed miserably, and felt like crap most of the time because no one told me about the flailing around part. After a year or two, I found my groove and things have been humming along well enough ever since.

So, I don’t know who needs to hear this, but I sure as hell did four years ago: “Hey! You’re going to flail around until you figure it out and that’s okay.”

Networking is Flailing at It’s Best

Despite trying and failing to follow all the advice in those early days, I did manage to do one thing right. I went to as many in-person networking events as I could. I was everywhere, man.

It wasn’t uncommon for me to go to three or more networking events some weeks. I never turned down an invitation to get coffee or have a discovery call and it really didn’t matter to me who was doing the asking. If opportunity was knocking, I was going to be home to open the door.

This was failing around at its best. It was my own personal version of heading West during the Gold Rush.

Yes, my “gold fever” policy landed me in a couple of awkward sales conversations with people trying to sell me things I didn’t want to buy. But even these conversations were valuable for teaching me what not to do (and how to say “no”). Overall, it would be impossible for me to understate the value of networking for building my business.

Here’s what I learned during those early networking conversations:

  • How to socialize with people in the business world
  • How to spot opportunities in every conversation
  • What questions to ask people to make them feel interesting
  • How to answer the questions I was mostly likely to be asked
  • How to talk about what I was up to in my business

When I say I miss flailing around and chasing down opportunities, this is what I’m talking about. I miss the thrill-seeking feeling of digging for networking gold — meeting someone new, evaluating where they are in my sales process, and positioning myself to provide value. When everything’s so new, it’s as if you can’t go wrong. You’re in discovery mode and mistakes are an important part of the game. It’s freeing and fun!

Now that I’ve figured out some stuff, the stakes seem higher. The temptation is to stick to what’s safe, to cling to what I know (or think I know). Sometimes, I wish I could go back to those days of flailing around.

Flailing Around is Good Strategy

If 2020 teaches us anything, I hope it teaches us that flailing around is a good response to chaos and uncertainty. I’m not flailing around unintentionally the way I did when I started my business. My flailing is more strategic now. I am open to intentionally put myself into flailing mode.

For example, one of my strategic priorities for my business this year is to be seen and to help others be seen. Plan A for getting seen was doing live speaking engagements. I gave my signature talk for the first time on March 8 in a hip little bar/black box theater in Raleigh, NC. I loved being on that stage.

Obviously, Plan A has been derailed, though. So I took the opportunity to make online networking, specifically on LinkedIn, more of a priority during the pandemic.

Here’s how I’m flailing around to be seen on LinkedIn:

  • Posting M-F each week since June
  • I have themes for each day (Mon. is biz strategy, Tues. is mindfulness, Wed. is promotional content, etc.)
  • I create my posts a week in advance
  • Engage with others for 20 minutes 2x per day

I’m also flailing by helping others be seen on Linkedin. I started a video interview series I’m calling the Own Your Expertise interview series. I use Zoom to pre-record or go live with entrepreneurs and ask them to tell their stories about their own path to becoming the experts they are. It’s my own little research project into entrepreneurial anthropology.

As a ghostwriter and an introvert, I’m more comfortable flailing around behind the scenes. But as a business leader, I’m also in a position to put my flailing on display and take some chances. And for the first time, I’m starting to feel this as a responsibility — something beyond merely a means to lead generation.

The proof is in the results:

  • Before this summer, all of my big fish clients came through referrals
  • Since I started speaking up on LinkedIn, I’ve gotten 3 ghostwriting prospects, one of whom became a client so far, and my pipeline is full
  • I’ve met many new people from around the world I wouldn’t have otherwise met
  • The conversations I have had have inspired me to create new content
  • All of this is expanding my big picture thinking about my business

Because I never know where my clients will come from, flailing seems like the right strategy. My goal is to meet as many people as I can.

Still, since the early days of my business, my philosophy on networking has evolved a bit. I’m more strategic about the virtual networking events I attend. I can’t see myself ever joining another membership based networking group where you meet with largely the same group of people every week. But I’m still open to meeting basically anyone for a (virtual) one-on-one coffee chat.

Flailing is maybe scarier than it was four years ago. There’s a big difference between falling off a cliff and intentionally jumping off a cliff. Four years ago, I was blissfully unaware of my flailing. Now, I’m aware that I’m flailing and my brain desperately wants to take control. I have to resist the urge to hide and flail in silence.

Here’s what I’ve learned as I’ve flailed around to find my footing with online networking in 2020:

  • I used to think that speaking up was only important for flashy businesses that need a huge volume of customers. But I’m really starting to think about how I can speak up and be seen by more people.
  • I used to see brand visibility as a tool for lead generation, but it’s about more than that now.
  • I’ve realized that I like inspiring people. I want to speak up and be more visible not just for my ghostwriting clients, but also for new business owners and academics looking to find a way out of academia like I did.

I’m also starting to think more intentionally about the spaces where I want to be seen and heard. Do the places (both virtual and IRL) where I’m showing up align with my brand’s values? Are the ways in which I’m speaking up helping me play bigger or making me appear smaller? It’s not where do I want to be in 5 years or 10 years? It’s what legacy do I want to leave behind?

We’ve all been wondering what kinds of permanent changes and ripple effects 2020 will leave in its destructive wake. I hope with time, we can also see how the flailing amidst uncertainty has been constructive both in our lives and our businesses.

Emily Crookston is the Owner and Decider of All Things at The Pocket PhD. She’s the ghostwriter for rebels, renegades, and mavericks. She loves helping experts who are long on ideas, but short on time write business books. Find out your writer type with her Writer Profile Quiz.



Emily Crookston

Emily Crookston is the Owner and Decider of All Things at The Pocket PhD. She’s the ghostwriter for rebels, renegades, and mavericks.