Why am I so bad at business

Why Am I So Bad At Business?

If you’re reading this because you Googled “Why am I so bad at business?”, take heed, you probably aren’t!

You’ve possibly created some bad habits, but who hasn’t?! So, despite the bad business practices, if you’re asking yourself, “Am I even business-minded?”, there’s hope!

I write today to emancipate you from your fear and stress, to discuss how to move on and be happy in your day to day business, and overall success.

I write this to show you why you need to let go to move on, but specifically, how you let go of the past.

Finally, I want to share with you some stories of entrepreneurs that have struggled and show you that you are not alone!

Bad at Bookkeeping

It’s cliche AF to say, “In the struggle you find your strength, and through the challenge comes the opportunity”.

As a small business owner, every damn day can feel like a hero’s journey. And yes, we learn and grow and stretch and succeed and fail and far out. 

I am exhausted thinking about it! 

So, how do we persevere and push on? When is it quitting time? What if we aren’t cut out for business ownership? What if we’re frauds and fuck ups and everyone is about to find out? 

Or what if we save the drama and scary stories for a campfire, and get back to business. 

Running a business is a lot like having a job, but instead, you have too many bosses to count! 

Your customers / clients / buyers/ employees & contractors, your vendors and service people, even your friends and family start to show up more like they’re in charge of your life and decisions.

(oh, just me?)

The thing is…….

*she says after cussing out her bookkeeping software, trying to run end of month processes and end of year projections*

It’s our struggle that makes it hard and our resistance that adds to the heavy-lifting.

It’s our stories and wishes of it being differently.The,“if-only-I-had-more-resources” mindset and resulting resentfulness. It’s the angry, fearful and avoidant feelings. Within these things,the hardships are created. 

So let’s unpack where our stories came from. Find out how acceptance and letting go of the past is crucial for success. Let’s learn how to let go and stop questioning whether or not you are bad at business.


I was tempted to title this blog, “How To Surrender”, but turns out that is the opposite of what anyone is seeking to do with their business.

Really, “surrender” has been hijacked by spiritual mumbo jumbo and a lot of those phrases make zero sense until you’ve done the work!

(ha! See what I did there?!)

What is Acceptance?

Acceptance is learning to not settle. It’s agreeing to not give up but understanding the scenario, processes, and or challenges to come.

Through acceptance, we make things easier and potentially more clear, allowing us to really step up and move through it. 

Most of us can relate to thinking the worst right away. We jump straight to the thoughts of “it’s going to be hard”, or  “suck”, or that you are going to fail (because it’s happened before).

We base the “what will happen?”on past experiences, and assume we will repeat the “what has been”.

Perhaps, that doesn’t have to be the case?

What if just because something happened before, that doesn’t mean it has to happen again? 

What if – and I am going to beat this bookkeeping analogy into the ground but that is EXACTLY the process I am avoiding by writing this blog – but what if bookkeeping doesn’t have to suck? 

What if my month end close process could go smoothly?

What if every time I do it, I choose to improve and roll with the punches? To look at the investigations and “why won’t this bloody account bloody reconcile?”as a Sherlock Holmes styled adventure? 

By spending just 30min doing the dang thing, I will get 90% of the way through it, and I can save the next 5-10 minutes for when I am ready to get it done. 

Accepting the situation as it is, without some dramatic narrative, means it just is.

It isn’t good or bad, hard or easy. It’s just another process to complete. Letting go of the past means that just because it happened before, doesn’t  mean it has to happen again. 

When we stop feeding our confirmation bias, (ie. the way our brain looks for evidence to support our suspicions), and instead we choose to look for evidence to the contrary.

(as in bookkeeping is simple, easy, and one of the quickest items to complete)

In doing so, we immediately let go of what is holding us back in this scenario and potentially every place we make assumptions.

Instead of avoiding and complaining about bookkeeping, I open quickbooks and get it done.

No, I won’t get the sympathy and “tell me about it!” from my fellow business owners and accountants.

I won’t get any extra attention from my staff or business partner, it just gets done. No fanfare. No drama. And on to the next thing. 

Oh, and one other thing, don’t let the make-believe, yet-to-happen future ruin your moment either!

This one is actually my favorite! I do it ALL THE TIME! I make up something that HAS NEVER HAPPENED, and then I worry about it SO HARD I can’t do the damn thing that inspired my imagination in the first place. 

Like, using the only analogy I am apparently capable of – bookkeeping and month-end close – what if I discover ALL my businesses are insolvent and I’m destitute? Or, what if I do it all wrong and the IRS arrests me? Um, what?

So, in 24 years that has NEVER happened. Ok, so let’s just set those stories aside, along with the assumptions about what has happened, so I can jump into this process and choose to make this task simple and effective … now go! 

Letting Go

Sounds so simple right?

Well, it’s definitely simple but, it may not be that easy. 

Our thoughts feel really true. Our emotions only reinforce that thought. If I tell myself this will end badly, and I physically feel afraid, I have to be right? Right? Maybe … 

This is why I love to refer to everything as a test. I am hypothesizing I won’t suck at bookkeeping, and I won’t ruin my businesses / life.

I’ll test this process and everytime the doubt and fear creeps in, I’ll politely set it aside, just for 30min.

I test the results. 

  • How do I feel? 
  • Do I accomplish my goal? 
  • If not, why? 

Turns out, bookkeeping and month end close for 5 businesses is about as simple as learning to let go. But it takes practice. And acceptance. 

Yes, I was able to efficiently and easily get through the process.  I did have some questions about charges and reconciliations, but I could answer those later.

I tested setting those aside and getting through as much as I could to complete the task at hand. Then I tested waiting until I wanted to dig into those questions.

Low and behold I had to sit on hold with our automated phone. VIP service for 30ish minutes. And I completed the process. 

It worked! 

Not only was it simple, it was easy. EASY! And I will lay the bookkeeping / MEC to rest here, because the process is done.

(just kidding, it’s an example I share later but, just stop reading if you hate it, I get it!).

I had spent hours complaining and avoiding and used this analogy to the point of annoyance, and in less than an hour, it was done. 

Here’s my step-by-step approach to letting go: 

  1. Before taking action, I ask, how will I know when I am successful in this activity? 
  2. Notice, what am I thinking? What am I feeling? If it’s anything other than neutral to good, go to step 3. If I am neutral to good, skip to step 4.
  3. Challenge my thoughts. Or set my thoughts aside and get back to answering question 1
  4. Define my metrics and timeline (as in, 30 minutes, reconcile all transactions, update financial reporting … oh shit! There it is again, sorry!)
  5. Test it! 
  6. Practice (aka. Repeat steps 1-5 until the activity / scenario is simple and gets done). 

Moving Forward and Finding Happiness

We’ve addressed  that you probably are bad at business because now you know how to accept and let go. You understand that the past and the future tend to influence our current situations despite merely being  thoughts and stories. So what comes next?

Let’s break down the real fear, how can we be happy and move forward even if our experiment fails. 

The experiment can’t fail.

If the test didn’t give us the results we seek, we learn. 

The success or failure isn’t determined by the expected result because we don’t stop there. 

The test simply gives us enough information to improve and try again.

Eventually, we get to our desired result, or we shift focus and test something else by asking a different question. 

book your free strategy call

Happiness becomes the byproduct of working on our goals and is an experience we notice when we’ve realized that definition of success.

It’s not what you feel 3 miles into a run it’s  what you feel AFTER the run.

 (yay! Not a bookkeeping analogy, but definitely the other activity I am avoiding, ha!). 

The gap between expectation and reality is where we feel discomfort.

We expected one thing and got another. When we approach that gap from a place of curiosity and learning, our experience changes. 

I would never suggest anyone settle on something less than what they want, or give up – ever, but when we understand acceptance and dare I say, surrender, it removes the struggle and suffering from our day-to-day. 


I am sure you’ve heard the Buddhist adage, “pain is inevitable, suffering is optional” and thought WTAF.

We can speak endlessly of  painful experiences and the sufferings we endured! 

Suffering gets us so much: we get attention, we get help, we get nurturing, we get understanding, we get patience……we get a lot. 

Sometimes we stay there, in the suffering, because we keep getting our needs met. And there’s nothing wrong with fulfilling our needs. 

The question remains, “How do we move forward from the suffering?”

The single step to moving and being happy, is knowing that we alone can fulfill our needs. 

When we ask ourselves what it is we really need right now, without judgment, we find our answers and discover how to be happy in any moment. 

Bad Business Practices Examples 

(AKA, Good Stories with Bad Feels, so you know you’re in Good Company because sometimes we all choose to suffer)

Ye Olde Bookkeeping Story

I have been playing with this idea and testing it within my 4 businesses, but also testing it with my clients and compatriots. 

Here’s the thing, when we drop the story – the “I hate this …” “I suck at …” “ I wish that …” and just do the damn thing, it’s actually not that bad. Dare I say, it’s just fine. 

Now “fine,” is one of my favorite four letter words. It typically means, I am compartmentalizing, avoiding, settling, and just moving on.

However, when the activity or conversation or learning is so big that “fine” is quite the leap, as opposed to scary, despicable, hated, etc. 


As I alluded to, I am supposed to be doing my bookkeeping.

It’s that time of the month when I run my financial reporting packages, reconcile accounts, review payroll, set aside income for taxes and savings, and generally spend a few hours “hating my life.”

My amazing, “choose-my-own-adventure life”. Um, what? 

It’s my story around this activity that sucks.

Honestly, the fact my 18 bank accounts can seamlessly integrate with accounting software, I click some buttons to reconcile, I digitally save receipts.

I mean, it’s basically black magic. I used to have entire filing cabinets filled with tax receipts and paper statements and blah blah blah. 

For the last few months, I have been holding myself accountable and asking, where is my story ruining my moment?

 Bookkeeping is one of the easiest things I do. Sure, it’s repetitive and monotonous, but so what?! It’s only my resistance that makes it difficult. 

The CoVid Conundrum

A client of mine works in events. Yeah, you know where this is going. 

When all public events were forcibly closed, sprinkled in with the fear and doubt that large gatherings would be a concern for safety; it’s easy for one to assume (past story) that we will never have large events again (make-believe future fear). 

Now, this client creates immersive, digital experiences at events. 

Think huge corporate events, public spaces, industry conferences, the types of events that 10,000 people or more filter through. 

Again, he could have chosen the whole “suffering” for months on end. Unfortunately he did have to make painful choices.

He furloughed and eventually let go of his team members. Shut down his studio space, and found himself in the role of business development. He got back to the basics of cold calling potential clients. 

However, this client chose to simply be in the moment. 

He reframed his pain as a way to learn more about his clients and industry.

He looked at cold calling, something every single one of us has a story around (and lots of eye-rolling and finger-in-mouth gagging dramatics), as a way to connect with other industry leaders and inspiring organizations. 

I’ll save you the gory details, because for this client, they were simple experiments with no drama or story, just processes to test in his business. 

There is a happy ending, a few actually. 

The moral of the story is, when you stop allowing past or future stories from curtailing your efforts in this moment, amazing things can and do happen. And they’re usually not anything we could have expected.

Now, instead of commuting an hour to / from his studio, he found a space 10 min from his home and literally 1/10th the cost of his pre-CoVid space.

He has refreshed his team and found new resources to specially address his business challenges. 

He reconnected and partnered with other experts to offer a totally new service and product to his clients. 

He not only rekindled client relationships, offering them a new solution to their now most pressing problem – how to connect anywhere but with an experience that far surpasses zoom.

And now, he’s working with world-renowned institutions who need unparalleled digital experience more now than ever! 

Had he given-up and said, “well, I do events and there’s no more events” he would no longer be in business.

The gap between his expectations, what he had planned for 2020, and what happened in 2020, was disappointing to say the least! 

By exploring that gap, and asking a different question, “what do my clients need now vs what they needed before”, he was able to test a totally new hypothesis and take some different actions to yield surprisingly desirable results. 

Bad at Business: The Final Example 

This year has taught us anything can happen. Really, that lesson and that reality has always been there, but this year we couldn’t avoid it (like I avoid bookkeeping and running! BAM! Ok, actually last mention, I promise). 

When you find yourself spinning out into extreme unformat, ask yourself why. 

  • What do you need? 
  • What if there isn’t any one to blame? 
  • What if everything that has happened to lead you to this experience doesn’t matter? 
  • What if you are in complete control of discovering your solutina and being successful in this challenge? 

What if you don’t have to feel “good” about it to get through?  

Just get curious. 

I know I choose to feel angry, resentful, sad, or any extreme to get attention. 

I want people to KNOW I am UPSET. 

Why? Um … uh … so they think this is a big deal?!?

But for them, it isn’t, and it perpetuates the scenario. 

What if You don’t need their validation? You are allowed to be upset, and by being upset and wallowing in it, You move through it to neutrality. 

Then You choose how you want to feel. How will you feel once you are successful. THAT. you want to feel THAT. So,choose that feeling, then act.

You’re not bad at business! 

That’s a story. You are committed to your success. I know because you read this blog! When you drop the story and embrace the moment, you can be as successful as you choose to be! Over and over again.

Test it, I dare yeah! And comment below, I’d love to know if this resonated with you. 

Lead and Manage Change Like a Boss

Leave a Reply

Your email address will not be published. Required fields are marked *