By Bryan Orr

Doggedness, Determination, Grit, Consistency, Resourcefulness

These are all traits that determine small business success as much as anything else, but there is a problem: Sometimes it’s time to move on, and for the stubborn entrepreneur, that can feel impossible.

So when is it time to hang it up? To move on to the next opportunity? I can’t give any hard rules, but as a guy who had a startup fail BADLY, I can give you advice that came from that experience and the experiences of many other business owners who have gone before.

Here are five telltale signs it may be time to quit your business and move on.

1. It Isn’t Growing

Some businesses take a while to gain momentum and some businesses really don’t require growth, but for most businesses, if you aren’t growing there is a reason. If you have extended periods of no growth you may want to look more closely into why that is.

2. You Aren’t Growing

When you find that you aren’t getting better, learning new things and being challenged in your work it can often be the first sign that you are losing interest. You may just need a break, some training, or a conversation with a mentor… or it may be a telltale sign to consider.  

3. It Isn’t Rewarding

Compensation isn’t all money; it can be free time, the ability to work with people you like, doing work you enjoy, and naturally, money. If your business isn’t providing those things, it may be time to rethink it.

4. It’s Not What You Set Out to Create

Tony Hsieh of Zappos talks about how the company he originally founded became something he no longer identified with as it grew. When it was a new business, there was a dynamic culture. When it became a big business, full of rules and policies, he could no longer relate to the business, even a business he had a big part in creating. He chose to leave, foregoing a big monetary payoff in the near horizon if he stayed.

5. Relationships are Suffering

If your friends and family are telling you it is too much, if those closest to you know it’s getting to you and separating you from them, it may be time to take stock of your situation. Sometimes it’s just as simple as asking those closest to you “Should I quit?” and then listen to what they have to say.

A Controversial Word of Caution

The #1 cause of stress and relationship trouble is money trouble. If you find yourself in a place where you need to take out ANOTHER line of credit to keep the business going, or borrow from friends, or refinance the house, etc, my advice would be: don’t do it.


There are the stories of lady who borrows $1,000.00 from her grandma and becomes a billionaire or the guy who takes out a second mortgage on his house to keep the doors of his business open and then builds a big brand. The trouble is that EVEN IN THE SUCCESS STORIES you may want to dig deeper and see what it cost them.

Mental health issues, broken relationships with children and spouses, siblings who are no longer speaking, employees who never got paid. This is certainly not always the case but it’s good to count the cost before you borrow that high risk money to keep your business alive another few months.

I took investment money from friends and family for my first web startup and I told them ALL it was likely they would lose money. They invested anyway. And lost the money.

To this day, accepting that money is my greatest regret in business.

Sometimes, quitting is the right decision.