Stay Ahead. Work Smarter. Live Free.

I am Stephen J. Bailey, The Stay Ahead Solopreneur™ — creator of Eliminate Meetings™ and a leader in helping entrepreneurs, solopreneurs, and corporate teams reclaim time, focus, and freedom while increasing profit.

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$7.2M SOLOPRENEUR

Est. 2006

A young man with short brown hair, smiling, wearing a black shirt against a dark background.

I burned out doing everything “right” — it was the wake-up call that changed my life

Over two decades of 70-hour workweeks and nonstop meetings earned me half a million a year, but left me exhausted and uninspired.

Post-pandemic, I burned the playbook. I built a seven-figure, solo business with no standing meetings, focused work, and a life that was finally mine.

Now I teach others to do the same, because success should bring freedom and joy to your life, not destroy it.

The Stay Ahead Solepreneur — My Story
Three people smiling and posing together, with a wooden background and some greenery.

I help driven solopreneurs, entrepreneurs, and corporate leaders work less and earn more — by staying ahead

Build intentional systems for your life that keep your career and business sharp, streamlined, and under your control.

This is how you run a business that doesn’t run you.

Create your new life. Let's connect!

The Stay Ahead Solopreneur — Notes & Noteworthy

Featured
Don’t Replace Revenue — Stack It (then Stack it Again)
Don’t Replace Revenue — Stack It (then Stack it Again)

This is how I went from zero clients to 30 clients in two years with no experience and no team.

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Make “Sunday Scaries” Your Moneymaker
Make “Sunday Scaries” Your Moneymaker

Trade anxiety, stress, and apprehension on Sundays for money, freedom, and the last laugh.

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“Staying Ahead” Handed Me a Six-Figure Solopreneur Career
“Staying Ahead” Handed Me a Six-Figure Solopreneur Career

In my first 18 months as a full-time solopreneur, I had tripled my previous Corporate America salary. By the end of year two, I was managing 30 monthly clients.

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What Is a Solopreneur? You Might Already Be One.
What Is a Solopreneur? You Might Already Be One.

When I found out what a solopreneur was, it hit me like a truck and explained decades of my life in seconds.

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“Stephen taught me so much about a subject I thought I was already an expert on: myself!”

—Jennifer F.

Bold white text on black background reading "ELIMINATE MEETINGS" with an icon of a calendar and an arrow pointing to 'go'.

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