Yom Kippur as Your Guide to Overcoming Business Mistakes

What does a perfectionist business owner do when she realizes she made a huge mistake and is now questioning all her life choices?

Well, if it happens to be the week of Yom Kippur when said mistake happens, she uses a millennia-old framework for repentance that is also a blueprint for overcoming mistakes in business and life.

The 4 Steps to Repentance

Teshuva, or repentance, is a process that all human beings need to engage in regularly. There is a standard of moral excellence all of us should aspire to, but we’re also human and we often (usually?) fall short of that. 

In Judaism, we have a set time of year when we focus on repentance and atonement as a community. Of course, individuals can and should work on self-improvement all through the year, but the Jewish New Year is a special time for repentance.

These are the four steps of repentance:

  1. Regret
  2. Leaving the misdeed
  3. Verbal confession
  4. Resolution for the future

Since this is a business blog, I’m going to explain how these four steps help me overcome some pretty big mistakes and missteps in my business over the years.


Regret is not guilt. Guilt keeps us mired in shame and self-destructive behavior, while regret acknowledges we made a mistake and looks for ways to improve.

You can’t improve if you don’t acknowledge that you need improvement.

But then you move forward — because just simply regretting what went wrong won’t get you anywhere.

Leaving the Misdeed 

In this step, you actually stop what you were doing wrong. You can feel guilty about doing something, but if you continue doing it, you clearly don’t feel very regretful! 

In a business context, say you procrastinate on social media too much in the name of “researching marketing content.” Realizing and regretting how much time you’ve wasted is the first step. Then you need to leave it behind. Just stop doing it!

I know, I know, that’s easier said than done. 

But before analyzing why you procrastinate, and strategizing how to become more productive, you first need to just. stop. wasting. time. Sometimes the nuclear option — like deleting Facebook from your phone or installing timers that restrict your social media usage to just a few minutes a day — helps you remove yourself from the misstep while you work the next steps.

Leaving the misdeed also means not dwelling on the negativity. Don’t keep beating yourself up over the mistake. You goofed up—it’s time to figure out how and why it happened, and set it right. 

Flaying yourself on repeat, questioning why you ever got into this business in the first place, or doubting your ability to deliver good work in the future are weapons of the perfectionist monster who wants you to stay paralyzed in fear instead of charging forward in imperfection. 

You can’t grow when you’re still stuck in the negativity, so leave it behind and move on to the next step.

Verbal Confession

Speech brings concepts and ideas to new levels of awareness and understanding, so the steps of Teshuva always require verbal confession of your misdeed. (In synagogues on Yom Kippur, the community reads the verbal confession together multiple times during the service, and it’s quite an emotionally charged experience.) 

In the context of business, I think it is important to have a group of business friends who can keep you accountable and to whom you can confess your business bloopers.

At various points in my business, I made some pretty bad client-facing mistakes. I’m talking about transgressions like ghosting a client after they paid for a service; causing an entire website to crash during a launch; and worse. 

Some of these mistakes ate at me for years before I shared them with my accountability group. And once I gave them words, they stopped looming in my brain like some gigantic ogres. I was able to shrink them to size, release them, and move on. 

If you don’t have business friends, you should find some! (I’ll be your friend if you want.) Barring an accountability group, you can try journaling through the mistake to release and let go of it. The written word may not be as powerful as the spoken word, but it still can provide a level of release.

You also might want to try some rounds of EFT tapping. EFT stands for emotional freedom technique, and it involves repeating certain statements while tapping on specific points on your body. A huge reason EFT works is the release that comes from verbalizing scary feelings — such as the feelings surrounding a failure.

Check out this intro to EFT here:

Resolution for the Future

Now it’s time to figure out why or how it happened and how to avoid it in the future. Here are some questions you can ask yourself to get the ball rolling on analyzing the event.

  • Was it human error or system failure? 
  • Do I or my employee/contractor need more training? 
  • Is there a tool I can start using to avoid this error in the future?
  • Am I under too much stress or too distracted?

With many performance mistakes, you might also have to ask yourself the brutal question: how does this mistake affect my client, and is there any restitution I need to make? 

That can look like issuing a refund, correcting your mistake “off the clock,” or making it right some other way. The main thing is that your client doesn’t suffer from your error.

In the scenario I mentioned above, where you constantly find yourself scrolling through Instagram instead of working on your business, you might want to start by just observing your habits for a few days. What are you supposed to be doing when you reach for your phone? What part of that task triggers you to want to procrastinate? 

Is it too tedious? (Consider outsourcing it, or analyze whether it’s really necessary.) Is it too hard? (Another vote for outsourcing, or maybe you just need some training.) Is there a deeper mindset issue there, like perfectionism or fear of failure?

True repentance means putting new systems in place to prevent you from repeating the same mistake again. 

And you know what? That’s the only way to really grow and evolve your business. 

As leadership expert Robin Sharma said, “There are no mistakes in life, only lessons.”

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