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?



Isabelle she/her

Seller Community Manager, Square

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Message 1 of 120
119 REPLIES 119

I have a few repeat customers but the only jobs that really make any profit are one-time big jobs.  And those don't come every day. This isn't the type of industry where the same person needs something done often. It's basically an emergency service so if something breaks, they call.  My customers aren't really individuals, they're other companies.  So I need to find a way to reach other companies.  I've mailed things out before but the return wasn't much.

Message 22 of 120

@DysonMechanical maybe you have done this or not, but have you tried asking the companies that you've built a relationship with and are servicing if they have other companies that they can introduce you to? Normally once you have a relationship with one small business, that will lead you to other relationships with other businesses. Just a thought...

Message 23 of 120

I don't know your field, so forgive any stupidity, but I have known a lot of self employed people and I have seen trends:


1) Presentation matters: a nice trucks sells

2) Do superior work and be reliable, especially for commercial clients

3) Charge what you are worth, even if it is above market


Message 24 of 120

I'm listening to Crushing It by Gary V. on Audible- in it, there are many real-time anecdotes of business owners from all sectors describing how they reach their customers on social. I recently listened to a man that owns a chain of quick car oil change businesses.  Nothing so sexy that makes you think Instagram will love this.. well- he made tons fo content and its really done a lot to grow his personal biz and his brand. I don't know a ton about welding and I bet that is the case for many people. I don't even know why I'd need a welder- so it my mind that's the perfect fit for social (love idea of TikTok for you)... teach us all about welding. 

Message 25 of 120

Improving my online shop sales. My business is such that I do really well at shows under the canopy, but no where near the same for my online shop. Only customers from prior shows have made online orders. I've even once had a show customer purchase more online while still at the show. I'm assuming this was a gift for friends or family. I use my online shop & instagram to get the word out, and think I just have to keep at it.

Message 26 of 120

Maybe you could try a referral program with people who find you at shows? Discounts to get them to introduce your products to other people, etc.

Community Manager, Square
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Message 27 of 120

Have you tried selling live on Instagram or Facebook? 

Message 28 of 120

tiktok is the best to sell

Message 29 of 120

Lack of people who are willing to work. I want to grow my business because I'm maxed out without hiring, but finding quality pet sitters who will work for $18/hour and are willing to work weekends and holidays is virtually impossible right now. So, instead of growing my business and expanding my client base and revenue, I have to refer potential new clients and hot leads to other people in my business who aren't maxed out yet. 

Message 30 of 120
Super Seller

Looking ahead as the business grows we need to improve employee retention.  Staffing looks to be the biggest challenge in the next year.

We are also in the process of ordering inputs for our spring and summer crops 3-6 months ahead of normal due to supply chain issues


Message 31 of 120

we have found a lot of success with perks.. for the younger people it's less about pay and more about environment and extras.. for us: we always have a stacked refrigerator, we buy lunch daily, we are generous giving our employees first dibs on the cool merchandise and if we see something we know they'll love- within reason- we gift it to them. 

Message 32 of 120

I always have said no matter what I'm doing I should be doing something else and where I'm at I should be some where else. Now after 31 years in this business and now I'm changing my Couse of businesses. I now own 4 business and partner in another.

I have a great group of people working for me its finely giving me a little break, I'm very lucky to have them. But the entrepreneur in me still keeps me up at night thinking and plotting my business. I'm just that way. I'm 64 and still tell people I haven't peaked yet. the fire is still burns but at the same time I'm ready to step back and maybe have a 4 day work week and spend more time with my wife. I have been though feeling guilty faze when I took off but I learning to enjoy life while I still can, so I have to balance it all out. As a former bull rider I love the adrenaline rush. Doing Business does not compare to the bull riding side of adrenaline so you have to adjust it. So entrepreneurs out there a piece of advices keep the fire burning and where to get burn out dig deep and fine a spark in your sole and fan it into a fire and keep going. And remember this winners do what losers don't do and successful people do what unsuccessful people want do. GOOD LUCK AND MAY GOD BLESS YOU.


Message 33 of 120
Super Seller

Trying to remember to do ALL of the things! There is just so much to juggle as one person. And if you're anything like me, there are always new ideas that you want to work on as well. The holidays always bring their own special brand of stress, but this year with the supply chain and the economy looking the way it does - it's extra stressful! I think we're all feeling the pressure!

The Violet Fox
Message 34 of 120
Super Seller

For us it's our impending off-season (winter in the frozen desserts business). In 2019 we made it to a stable place, but we're still down post-pandemic so this one will likely be challenging. Last year we added a holiday retail section to help boost sales. This year we are doing it again, and I think we are going to try launching an app (looking at Orda), so we can capitalize on streamlined coffee sales for the morning commute. 

Hang in there, everyone! 

Michelle Leddy
Owner, BRRZAAR Cafe & Frozen Dessert Bar
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Message 37 of 120

Let's Go Brandon!  How quickly can an administration destroy an economy?  Pay people not to work, silence free speech, destroy supply chains, spike inflation from infinite government spending, open borders for illegal immigrants but put the screws to American citizens, gasoline prices through the roof, small businesses tasked with enforcing illegal mandates... once again, I'm up at night because of Let's Go Brandon!!!  This is not a good environment for running a small business.

Message 38 of 120

If there's anything I know after being an entrepreneur for a decade, running two different businesses.. and coming from a family of entrepreneurs.. is that economies and market conditions cycle. Now, I don't know anything about your business - but from  my experience we have over the past year increased sales 30% and we still have almost a whole quarter left. We have a waiting list of people that want to work for us- and we've adjusted our ordering to compensate for delays due to supply chain. There are issues in our beyond that we can and cannot control- I suggest focusing on what you personally can do in business.. not on forces outside of your control.

Message 39 of 120

i agree! sometimes i think is it even worth it anymore, do i close now before anything gets worse or push through hoping things will change, when in reality i see nothing changing in the future

Message 40 of 120

Currently,my lack of orders and site traffic. 

Message 41 of 120

I feel this one too! I put so much time and effort into the website and just feel it isn't reaching the right people. I think SEO has alot to do with it, would be so much better if the website (weebly) and (square) offered a better seo option! Tired of raking out money with no return! ~ Lisa 



Message 42 of 120