How do I keep going when it gets hard?

Nobody taught you how to run a business, yet here you are running one anyway. Some days that’s hard, and it’s supposed to be.

These answers are for the days you doubt yourself, feel stuck, feel alone or think about quitting. The last one is a real option, and it’s okay to look at it honestly.

Start here: Are You Thinking of Quitting Your Business For Good?

Every answer on this

• Are You Thinking of Quitting Your Business For Good?
  I want to quit my business. How do I know if I should?
• Why Being A Sole Entrepreneur is The Loneliest Profession
  Why does owning a business feel so lonely, and is that normal?
• How I Stopped Second-Guessing Myself (and You Can Too)
  How do I beat imposter syndrome and stop doubting myself?
• Feeling Stuck in Business? Here Are 4 Simple Ways to Pivot and Get Moving Again
  My business feels stuck. What small shift gets me moving again?
• Overcoming the Urge to Quit: Insights from Entrepreneurs
  How do other owners push through when they want to give up?
• Should I Ask a Question That Sounds Dumb?
  Is it okay to ask other owners a basic business question?
• Why Your Business Differentiator Is Worthless Until You Believe It
  How do I actually believe I’m good at what I do?
• Creative Bravery Never Gets Easier
  Why is putting myself out there still scary, and how do I do it anyway?
• Pressure is a Privilege
  How do I handle nerves before a big pitch, launch or price increase?
• Better Plans Won’t Grow Your Business, Behavior Change Will
  I keep saying this year will be different. Why isn’t it?
• The Luck Surface Area Concept for Small Business Owners
  How can I create more lucky breaks for my business?
• The Jeff Bezos Strategy: Betting On What Will Never Change
  Everything keeps changing. What should I focus on for the long haul?
• How Do I Know If I’m Working on the Right Problem in My Business?
• How do I keep going when it gets hard?
• I feel alone running my business. What should I do?
• Why working for yourself beats a job

From the show

• What a Small Business Conference Actually Does (September 21, 2026)
• Five Reasons You’re Not Doing The Thing (September 8, 2026)
• How Do I Create My Own Luck in My Small Business? (March 17, 2026)
• How Do I Know if I Should Keep Going on a Business Goal? (March 12, 2026)
• What to Do When Your Business Is Finally Going Right (February 23, 2026)

Questions owners ask

How do I know if I should quit my business?

Ask whether the business is getting you what you want out of life. If working for someone else sounds good instead of awful, it may be time to move on, and that’s okay. Read: Are You Thinking of Quitting Your Business For Good?

Why does owning a business feel so lonely?

Because the people around you usually don’t see the risk you carry every day. That’s normal, and it’s why owners need other owners to talk to. Read: Why Being A Sole Entrepreneur is The Loneliest Profession

Is it okay to ask a question that sounds dumb?

Yes. Ask it. Other owners have almost always asked it before you. Read: Should I Ask a Question That Sounds Dumb?

More topics: What you sell · Getting clients · Pricing · Money · Hiring and handing off · Time and burnout · AI

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