Dear Discouraged Business Owner

On December 6, 2013

Dear Discouraged Business Owner

Dear Discouraged Business Owner,

Being a business owner is not the easiest thing in the world.  It isn’t the hardest thing in the world either.  Everything in life comes with the ups & downs, but after spending a week on the phone with business owners, I wanted to write this note.

I feel you.  As we speak, I don’t feel like the most successful person on earth.  Sure, we have some good businesses running & my family is doing well at the moment, but there is still a little bit of discouragement present.  You know what it’s like… The weight of:

  • Cashflow management & payroll
  • Insurance premium increases
  • Tire kickers who say they want to buy, but don’t & waste your time
  • Your leadership being under a microscope
  • Not being where you thought you would be at this point in your business or life
  • Uncertainty. Constant uncertainty.
  • People you know you need to fire, but you just let them hang around
  • Knowing your company isn’t perfect
  • Trying to give people great opportunities, but they don’t seem to appreciate it
  • People letting you down
  • You letting yourself down
  • Seeing other people’s businesses & keynote speeches & believing they have it easier than you do
  • And on and on and on it goes…

This is the side of owning a business they don’t teach you in business school or get rich quick courses.

I want you to know something.  The discouragement you feel inside is real & coming from somewhere.  I read this one time & believe it’s true for you & me,

“The happiest & healthiest people are those whose expectations meet reality.”

Here are four questions I want you to ask yourself:

1. What do I expect my business to give me? 

No business will ever give you peace, fulfillment, joy, purpose, or anything like that.  If you are expecting that from being a business owner, you won’t find it.  If you are constantly discouraged or frustrated about your business, it might be because you are hoping it will give you something only God can give you.

2. Who am I trying to please? 

You will never please your employees fully.  It’s impossible because we are imperfect people & they are as well.  If you are trying to please other business owners or coaches in your life, you will be miserable.  You can never keep up with anyone else’s expectations.

3. How honest am I being with myself & others? 

If you stuff your business failures & missed expectations instead of dealing with them, you will explode one day.  Your discouragement & mine often comes from stuffing things we should just admit.  If you have a problem with a business partner, be brutally honest with them.  If you are mad at somebody, tell them.  If somebody let you down, let them now.  If you have let yourself down, tell a friend.  Lying and pretending leads to misery.  Just say it.

This is why I hire coaches & go to a professional counselor.  If I didn’t, I would burn out & implode.  

4. What lie am I believing? 

Gurus make it seem so easy don’t they?  Buy their course & you will have a lot of money & freedom.  Ever bought into that lie?  Did you think owning a business would be easier?  Well, that’s just a lie.  Identify the lie you are believing & you will crush some of the discouragement.  The lie that marketers sell you is really killing your spirit.

Your discouragement isn’t just discouragement.  It’s a symptom of something deeper going on.  If you want to create a healthy business, you can’t live mad all the time.  You can’t be frustrated 24/7.  Take a step today & answer these questions honestly.

I believe it will help you beat your discouragement & get back on the growth track.

Comment Question: Have you ever felt discouraged as a leader or business owner or am I the only one?  Any tips or strategies you would give on how you deal with it? 


  • By caseygraham  4 Comments   1


    Posted by Jessica Freeman on
    • Dec 6 2013
    I do get discouraged, mostly when my things don't sell. But, as my husband reminded me this week... I'm doing what I love. I'm sharpening my design skills, I enjoy doing these projects, and my "products" are not our source of income by any means. It's still discouraging, to not have someone take enough interest in your stuff to buy it... but I try not to focus on it. :)
    Posted by Julie Gordon White on
    • Dec 6 2013
    I try my hardest to stay present and enjoy the journey... somedays are WAY harder than others!
    Posted by Richard on
    • Dec 9 2013
    Stop reading my mind Casey Graham! The lie I'm believing is the "overnight success" lie. Why is it so freakin difficult for me but so easy for everyone else.
      Posted by Allan Spragg on
      • Jan 12 2014
      Hey Richard Imagine me. A pastor and business owner. Neither one are easy, neither one are an over night success, far from it and neither one define me. I am still working through all of these, to be very honest. The one thing I find helpful are people like you who understand and a God who clearly understands. May His peace and courage be yours. Stay vulnerable, stay in love, be realistic and hopeful.

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