On Listening as Leadership (and why it matters for entrepreneurs)

Friday night, my old iPhone died a sloppy and long overdue death. It was a blessing in disguise, as it prompted an unscheduled phone-free writing and brainstorming weekend. I finished two novels I’d been re-reading, had a record-powered dance party, wrote a ton, and on Sunday, I picked up Hillary Clinton’s book on her experiences in 2016, What Happened, at the local Goodwill.

It got me thinking about a communications analyst I heard explain one of the societal issues that contributed to her defeat (aside from the more obvious, ahem, anomalies).

He said, the American election system was created by men, for men—and for male communication & leadership styles. It’s not about being the best leader, it’s about being the loudest.

Secretary Clinton’s campaign style, on the other hand, centers around the opposite: she listens. Several leadership experts have written about her style since her first 1999 Listening Tour, and 'listening' is not just a campaign style: it's a revolutionary kind of leadership.

The most common leadership style, transactional, is exactly what you’d expect from an old-school sales manager: an exchange. Rewards for compliance, punishment for failures. Think bonuses, promotions, demotions, etc. Academics have recognized this as the typical male model of leadership in organizations since at least the 90s.

It’s effective, sure.

But if you’re an entrepreneur, chances are you’ve felt the stifling lack of creativity in many jobs & organizations… and bailed from it. The zero-sum exchange game has a way of snuffing out new ideas, growth, and transformation—especially when those ideas come from an “atypical” perspective (hi, women and minorities everywhere).

It’s no surprise, then, that so many of us are working & searching for a different path. A path that values transformation, ideas, and creativity. A path that lets us take the reins back and breathe in the life-giving air of creative expression.

But as an entrepreneur, even working totally solo, you still need to /lead/ to be effective. You’re selling ideas, influence, and change. So what’s the alternative to bald-white-man leadership? (yeah, I went there)

Enter the transformational leader.

The transformational leader is an agent of change who can influence the outlook and actions of her audience.

Rather than forcing her idea of success on followers, she develops a strong sense of vision to clarify and communicate objectives to motivate, encourage commitment, and inspire action.

In a presidential candidate, these objectives are those of the country. In a CEO, it's the organization. For the rest of us? Organization = community.

To truly lead people to change & grow with you, you must clarify and communicate your vision, and build a relationship with your community around creating that vision for yourself, your audience, and the world.

And of all the skills you need to build relationships, effective listening is the most important, for Hillary Clinton and for every relationship coach, travel advisor, and copywriter on the web.

A listening-first approach offers its own rewards, even for solopreneurs on the intarwebs. Imagine… 

  • Earning that “know, like, trust” factor faster than ever… even as a stranger on the internet.

  • Inspiring your audience to take action, instead of scaring them off by asking for the wrong sale at the wrong time.

  • Creating client experiences that meet & exceed expectations, every time (so you always get great reviews & client love).

  • Having your words shared and loved by the /right/ people (the ones you really care about).

That’s the power of listening. Because if you’re listening, your work is part of a conversation, not a shouting match.


On having an expensive hobby instead of a business

I spent a couple of years “building my business” on the side while I worked a corporate communications job.

I’d get up at 5 a couple times a week and write a blog post, schedule social media content, adjust my website copy, and create all kinds of design downloads, templates, and sales pages.

But all those months of researching, designing, studying, writing… I never made a penny.


Within two weeks of leaving my job to travel, I was settled in a house sit high in the Sandia Mountains of New Mexico, and I was on the phone with the women who would become my first two clients.

In the last month of my job, I had already put in my notice, so I knew everything was on the line.

I designed it that way. I knew I didn’t have a single client yet—It was a risky move. Even though I let them believe I already had clients, my friends and family thought I was crazy. If they had known I didn’t even have any paying clients yet, they probably would have put me in a padded room.

But I had a feeling. I knew I was never going to make a change unless I absolutely had to. I was unhappy in my job, and not making progress in my business or writing. So I bet everything that I could do it, leaving myself with one option: doing it.

I didn’t know it yet, but that’s when everything started to change.

I realized I was missing… so many obvious steps. At the time, I believed some version of “If you build it, they will come.” I was trying to do it all myself, and instead of making connections and building a network, I was just trying to build a list. I was afraid of reaching out and talking to real people—because I’d have to either admit that I’d never had a client, or feel like a fraud calling myself a ‘copywriter and marketer’ when the only marketing I’d done was free & volunteer projects.

(Lists are great and incredibly valuable. But a list all on its own is like a diamond without a ring setting. It’s pretty, but what in the world are you going to do with it?)

Once I had no other income, that fear didn’t go away. It simply became irrelevant next to the absolute requirement that I find money for groceries and gas to get to my next house sit.

So I started connecting with people—As Ashton, the writer and marketer, not Ashton, the corporate employee sneaking around trying to start a business.

I helped out a few well-connected people in my ideal client group with free strategy, then I asked them for referrals. I began selectively cold-pitching others with personalized emails, shoutouts on social media, and offers to serve.

I actually stood behind “I am a copywriter and marketing strategist.” And the more I said it? The more opportunities I got to go out and BE one. The more I said it, the truer it became.

Today? I can’t imagine it ever not being true again.

On having 1.6M Instagram followers & being "lucky"

Do it for the gram

I have a friend who runs a massively popular Instagram account. She and her partner have worked incredibly hard, consistently, for two years to build it to 1.6 million followers—and now, they’re able to leverage that work to provide both their full-time incomes.  

But the other day, when I asked her about an instagram tool I was considering, she worried  “It might sound annoying, but we’ve been really lucky, and haven’t needed anything like that…” 


I’ve seen how hard they both worked for that success—what they gave up for it. How creative they’ve been. The bad days, the legal issues, the hangers-on, the pivots they’ve made to keep being the best.

I haven’t seen those days for you. Maybe you’re still in The Hard. Or maybe the connections are starting to fall into place. But I have some advice to file away until the day someone’s asking YOU: “How’d you do it?” 

Feel no guilt when it comes ‘easily.’

There will be hard days again. Don’t waste the smooth days feeling like you don’t deserve them.

You deserve them. 

Things are flowing because you’ve put yourself in the right place, at the right time, and built the right skillset to make it work.

Because you took risks. Because you were open to possibilities. Because you asked. Because you worked.

“Lucky” is what people call you when they see you on top, but they can’t see all the scaffolding you built to capture that rooftop view. 

When you were struggling, you could see people succeeding. Their success didn’t make you smaller. When you’re succeeding, you’ll still see others struggling.

Lift them where you can, but don’t make yourself smaller for their comfort. 



Photo courtesy of Glen Anthony via Unsplash.