There’s a myth in the speaking world that opportunities just show up when you’re good enough.
They don’t.
If you want consistent stage time, you have to accept something that surprises a lot of talented speakers:
The speaking business is a sales business. Not pushy. Not transactional. But intentional, relational, and proactive. Because great talks don’t build speaking careers — outreach does.
It’s Not Just Who You Know — It’s HOW They Know You
You’ve heard, “It’s about who you know.” But the real question is: WHAT are you known by WHO for?
When someone is looking for a speaker, you want your name to instantly connect to a clear identity. For me, that identity is simple: I’m the WinAnyway Guy. Resilience. Ownership. Showing up when it’s hard.
Outreach reinforces that identity over and over so when the opportunity appears, you’re the obvious fit. Because if people can’t quickly describe what you do, they won’t think of you when it counts.
Visibility Beats Talent More Than We’d Like to Admit
I’ve coached incredible speakers who struggled to get booked. And I’ve seen solid speakers stay busy year-round. The difference? Visibility, consistency, and benefits-led communication.
You can’t get chosen if you’re not top of mind. And you don’t stay top of mind without ongoing outreach.
The 360-Email Breakthrough
One of my clients recently landed a major breakthrough client. It didn’t happen because of one perfect pitch. It happened because of persistence. He sent 360 outreach emails before the right opportunity hit.
Not spammy. Not desperate. Just steady, professional, value-focused communication. That’s what most people never see behind a “sudden success.” Breakthroughs usually look sudden from the outside - but they’re built on consistent outreach behind the scenes.
Consistency Beats Intensity
A lot of speakers treat outreach like a burst of motivation. They send messages for a week… then disappear for months.
Outreach isn’t a campaign. It’s a rhythm. A few touches each week does more for your career than one big push once a quarter.
Because consistency builds: Familiarity, Trust, Credibility, & Momentum!
Outreach Is Service, Not Self-Promotion
If outreach feels uncomfortable, it’s usually because it feels like self-promotion.
In truth, you're helping event planners succeed. Helping audiences grow. Helping organizations move forward.
You’re not chasing stages. You’re offering solutions.
The Bottom Line
If you want more speaking opportunities:
- Accept that speaking is a sales business
- Get crystal clear on your identity
- Stay visible through consistent outreach
- Be persistent enough to outlast timing
Because speaking careers aren’t built on talent alone. They’re built by people who keep showing up, keep reaching out, and keep moving forward…
Let’s Talk
If you’re working to get booked more consistently — or you’re trying to turn your message into a real speaking business — I’m always happy to compare notes.
Message me here on LinkedIn or reach out to schedule a discovery conversation. Let’s figure out your outreach strategy and speaker identity so you can create the opportunities you’re capable of - and Win & Speak Anyway!
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