As a business owner, what is currently keeping you up at night?

Hey Seller Community 👋 


Today's question is...


As a business owner, what is currently keeping you up at night?



Olive, she/her

Seller Community Manager, Square

Learn about the Super Seller program!
Message 1 of 126
125 REPLIES 125

Figuring out if my website is good enough and brainstorming different ideas to bring residual revenue 

Message 106 of 126
Super Seller

How to get new inventory of accessory items when they are not made in USA and its floating in the Pacific. How to make more of the items we make in house for these upcoming holidays when no one wants to work or expects a fortune to start with no experience.  When my parts will be available to fix a few of my broken wax melters.  How to keep all my inventory in check between online store, Square and Quickbooks.  I do not use Square's online Weebly site.  But I think my biggest frustration is my partner and her 'I will do it later' philosophy .... and making hand made items for decorations instead of selling them.  People love her hand made items and then she says those are not for sale.... I am like sell it and make yourself another one.  LOL  Especially when we sell similar items.


Now what keeps me motivated, My gross sales have tripled from what the previous owners had the store at in 2018... I bought it in June of 2019....and the gross sales are above 2020 and we are getting more people through the door than last year at this time.

Pocono Candle

Mark as Best Answer if this Helped you solve an issue or give it a thumbs up if you like the answer.
Message 107 of 126
Super Seller

Staffing Staffing Staffing:  How to get good people and take care of them.


How to not sacrifice standards when faced with hard choices.


When can I focus on growth more than conservation (maintaining a lean lean operation).


Those are my big three to tackle....


Personally, where do I see myself in 5 years.



Message 108 of 126

OMG everything. I opened a shoppe seven months ago and I'm drowning. We do classes and workshops in addition to the retail part. I am a jewelry artist so I supply the bulk of what I sell, plus ordering and managing other local artists I've invited to the space. It's a lot. Most days I am happy there, but I never feel I am doing enough. I can't afford to hire anyone so it's all on me. Most days it's completely overwhelming. I average four to five hours of sleep a night, and it's restless at that. It's good to hear I'm not alone, because I mostly feel alone. 

Earthy jewelry for body, mind and spirit
Message 109 of 126

🫂 Let us know if the Community can help in any way. Thank you for sharing @piecesofjayde 💕

Olive, she/her

Seller Community Manager, Square

Learn about the Super Seller program!
Message 110 of 126

What keeps me up as a small business owner, honestly is EVERYTHING. The fact that I should be working more, the fact that I feel I should be in more time organizing all that I have to do for the day. I feel like I should always be at my shop. A ton of things keep me up at night. Running a beauty salon all by your self isn't the easiest but this is only my first year, and I know things will become much easier with due time. 

Message 111 of 126

The VA (Veterans  Affairs) have failed to pay for 50% of the treatments I have provided and often dont send an EOB.  If I dont submit within a few days, I lose the money for good.  Since they dont send and EOB. I have to watch the mail and my square appointment software to see how much money is missing.  I am working 2 full time jobs.  My clinic and a corporate job.  My corporate job is funding my clinic since the VA is failing to pay.

I dont know what to do.  Can I send the VA to collections?  We are talking over $10,000 is missing payments that I had to fund out of my own pocket.  How do I work this loss on my taxes when I am not even issued an EOB explaining why I am not getting paid?  Should I even keep my own business open?

My quality of life is zero since I am working 7 days a week and often 12-16 hour days.  

I love working with the vets and I think that is where my entire 13 years of college and training really gets to brighten.  I dont want to give up on them, but I fear I am losing my self and my life to help them - and it is not their fault.

This is what keeps me up at night

Message 112 of 126

As a  business owner am always up at night because I am always thinking about how to grow my business bigger and thinking about new inventions I be up sending out tracking numbers to my costumers I be packing orders and keeping things updated am always up doing something.

Message 113 of 126
Beta Member

Hi mslisalive here.  I'm a visual artist, abstract paintings mostly.  I just love creating stuff.  Yes I used to be a chronic work-a-holic.  Then I found myself, meditating more and somehow, I found I'm more balanced, centered and focused... but I still have a great deal of fine tuning and adjusting to accomplish:  as within, so without.  


Message 114 of 126

Irritating surveys.

Message 115 of 126

Doing things right. Understanding the legal side of business owning so that me or my business doesn't ever end up under attack from any agency. 

Message 116 of 126

right now..................the Red Sox

Message 117 of 126

😬 Sorry 😢 

Olive, she/her

Seller Community Manager, Square

Learn about the Super Seller program!
Message 118 of 126

the awful state of the online store and the lack of listening to the community that the team does.  Also the amount of work its going to take me to transfer my business elsewhere.

Message 119 of 126

My snoring wife.

Message 120 of 126

😂 I suggest earplugs or white noise sounds

Olive, she/her

Seller Community Manager, Square

Learn about the Super Seller program!
Message 121 of 126
Beta Member

The fear that Square will change the POS interface again with no planning and notice like you did a few weeks ago and that Square won't be expeditious in fixing some of the bugs that came along with it. Our POS is the backbone of our business - when there are issues it affects my staff, my customers and my revenue.

Message 122 of 126

Trying to come up with new and innovative advertising for my cleaning company. 

Message 123 of 126

Staying consistent with content and reaching more customers. 

Message 124 of 126
Beta Member

The future of events, my target audiences finances and how the pandemic will impact my business model.

Message 125 of 126
Super Seller

As a small business owner, the thing that keeps me up at night is imposter syndrome. It's real! Some days I feel like everything is going great and then there are some days when I question my every decision. I have to make sure that I give myself mental space and try to catch it when it happens. 

Holly Coley
Message 126 of 126