Entrepreneurship is 3 AM thoughts that won’t let you sleep—and 7 AM responsibilities that can’t wait.
“Entrepreneurship isn’t lonely because you’re alone—it’s lonely because so few truly understand the weight you carry.”
The Silent Struggle: Breaking Through Entrepreneurial Loneliness
If you’re online at 3 AM, I already know what’s happening in your business.
I ask entrepreneurs that all the time.
Because when I see someone online at 11 PM… or grinding at 3 AM…
I know what’s going on.
👉 Trying to cover payroll.
👉 Figuring out taxes.
👉 Filling shifts when someone calls out.
And in those moments—it feels like you’re doing it alone.
Last week, during the entrepreneurship panel at VetsFest at the Georgia Aquarium, I spoke about this exact struggle.
The problems feel unique.
The silence feels heavy.
But the struggle?
You are not alone.
Takeaway:
The next time you’re up late with your thoughts, write down one name—a fellow entrepreneur, a mentor, or a peer—you could text or message the next morning. Look at the timestamps on posts or emails—those people are just like you. Or better yet, join a group like IVMF, Bunker Labs, or Tech Village and drop a message in the chat or Slack channel. That small step shifts isolation into connection.
Not just the panels or the networking. But the real magic happening in the spaces between—veterans helping veterans execute, not just dream.
One conversation turning years of paralysis into action.
One post connecting strangers into collaborators.
One minute of courage creating momentum that will last years.
Why Entrepreneurship Breeds Isolation
The loneliness of entrepreneurship is different because:
The Weight of Constant Decision-Making → Every choice ripples through your business, your team, and your family’s future (Wiley Online Library).
The Absence of Support Systems → You’re the CEO and the janitor, the strategist and the salesperson. There’s no HR department for you.
The Misunderstood Journey → Friends and family mean well, but “why not get a stable job?” doesn’t help when you’re chasing a vision.
The Pressure to Appear Strong → We’re expected to be resilient and unshakeable—so most hide their struggles instead of sharing them.
The Real Cost of Entrepreneurial Loneliness
Loneliness doesn’t just hurt emotionally—it hurts the business. Research shows it impairs decision-making, reduces creativity, and increases risk-aversion (Shopify).
Loneliness doesn’t just hurt emotionally—it hurts the business. Research shows it impairs decision-making, reduces creativity, and increases risk-aversion (Shopify).
Takeaway:
If you’re feeling stuck, don’t make big decisions in isolation. Before you act, share your thought process with a peer, mentor, or trusted advisor. Just talking it out often reveals blind spots—and lifts the weight off your shoulders.
Breaking Through: Practical Strategies That Work
The good news: loneliness doesn’t have to define your entrepreneurial journey.
Here are strategies—tested by myself and countless others—that actually work:
1. Build Your Personal Board of Directors
Every entrepreneur needs a circle:
The Visionary (sees possibilities you don’t yet see).
The Devil’s Advocate (keeps you grounded).
The Cheerleader (reminds you why you started).
The Fellow Traveler (another entrepreneur walking the same road).
Don’t wait for this to happen by accident—seek it intentionally.
2. Find Your Community of Belonging
There are organizations built to make sure you don’t do this alone:
Institute for Veterans and Military Families (IVMF) → A powerhouse for veteran entrepreneurs with training, networks, and mentorship.
Bunker Labs → A nationwide nonprofit helping veterans and military spouses build businesses through peer support and programs.
Tech Village → A collaborative hub for entrepreneurs and technologists where connection and resources are built into the culture.
Local Founder Networks → Many cities have entrepreneur groups, accelerators, and co-working hubs—places where showing up leads to belonging.
3. Change Your Physical Environment
Isolation grows in basements and back rooms. Try co-working spaces, coffee shops, or shared studios. Proximity to others often sparks creativity.
4. Leverage Technology for Real Connection
Instead of doom-scrolling, use tech to engage intentionally—join entrepreneur Slack groups, veteran founder forums, or structured online masterminds.
5. Reframe Solitude as Strategy
Not all alone time is loneliness. Solitude with intention can sharpen focus and fuel creativity. Learn to separate productive solitude from toxic isolation.
Breaking Through: Practical Strategies That Work
One conversation doesn’t solve every business challenge. But it reminds you that you’re not failing—you’re human.
Takeaway:
Pick one community today—online or offline—and make a post, send a DM, or raise your hand in a chat. Don’t wait for connection to find you. Create it.
Moving Forward Together
VETSFest 2025
Entrepreneurship will always involve sacrifice, hard choices, and long nights. But loneliness doesn’t have to be the price you pay for building something meaningful.
The entrepreneurs who thrive aren’t the ones who try to carry it all alone—they’re the ones who build systems and community around themselves. They know vulnerability isn’t weakness—it’s strategy.
So the next time you’re up at 11 PM staring at your screen, remember: there are thousands of other entrepreneurs awake too, facing the same doubts and the same dreams. You don’t have to do this in silence.
Takeaway:
If this resonated, you’ll love my newsletter Alternative Programming — where I share weekly insights on mindset, systems, and AI for entrepreneurs who refuse to do it alone. Subscribe here → https://alternative-programming.beehiiv.com
And if you’re ready to stop building in isolation and start scaling with systems, join us at the Entrepreneurs AI & Automation Summit in Atlanta on November 13th. It’s a full day of strategy, systems, and community — built to help you grow and scale smarter using AI. Secure your spot here → https://entrepreneuraisummit.com
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Building success together,
John Thomas
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