What is the hardest decision you’ve had to make for your business? 💭

Mornnninggg Seller Community! ☀️ 


Today I'm wondering...

What is the hardest decision you've had to make for your business?


What made it the most difficult? How did you come to the decision?





I look forward to reading your replies

Isabelle she/her

Seller Community Manager, Square

Learn about the Super Seller program!
Message 1 of 67
Super Seller

Few years back I was trying to decide about taking on a business loan to expand what I offer in the shop. Up until that point I was completely debt free in the business since I started it with cash I had on hand. Basically it boiled down to deciding if the debt would actually improve cash flow or not. It did gain a fair amount of customers so was worth it. Still wish I didn’t have the debt load though 

Message 2 of 67

Debt is always good when you have a plan, and the right investment. Money comes from debt. 

Message 3 of 67
Super Seller

All of the hardest decisions I have ever made date back to my previous Corporate life.  Some were good decisions and the bad ones were limited but one involved a decision to leave that was a little premature.   I really regretted that decision but now it is simply in the rearview mirror.

Today, as both the founder and owner of a growing and developing business all decisions are mine.   I make good and bad decisions for our business but I live comfortably the results.

Message 4 of 67
Super Seller

Similar to @homeprogreen decision, I would say that probably the hardest decisions that I continue to make are what products and services to offer.  I don't want to be like any other auto body shop, or online parts store, so carrying and offering select products and services that I specialize in, while also expanding slightly to gain more revenue from other areas.  Its a fine line to walk but its working well thus far. 

Scorpion Coating Plus,LLC
Square Super Seller
Check out Square support center for additional help.
Message 5 of 67
Super Seller

8 years ago I had to make a decision to either drop all my farmers' markets, except one, to focus on consumer and business deliveries. Or stay with all my markets. My thinking was I might make more money with deliveries rather than staying with 11 markets. I did switch to one market and deliveries and it turned out way better than I ever expected.

Life is too short to eat boring cheese.
Message 6 of 67

About a year before the Great Recession came crashing down, we had opened our second store (same town, one store a little out of the way, the new one right downtown). It was my ultimate dream space: beautiful, charming, great location. Also way more expensive; much bigger overhead (but the numbers bore it out). We were doing very well and growing like crazy. Until we weren't. After the crash, people simply stopped spending (especially on home accessories/gifts). And our landlords were less than helpful in working out a survival plan (unfortunately, they owned a number of buildings in town and didn't give their tenants any bit of leeway, as others did). So, with huge sadness, we decided to break our lease, sell off most of the inventory and fixtures, and retreat to our original location (much smaller, decent rent, kind and understanding landlords). Breaking the lease was horribly expensive, but we figured it was our only chance, short of going bankrupt. That was an agonizing decision. After that, I swore we'd never sign a five-year lease again. A dozen or so years later, we're still at our original location, doing very well, still keeping expenses down, and also sleeping at night. Since then, we've been operating on three-year leases with an option to renew and it's worked out just fine.

Message 7 of 67
Beta Member

I started a pizza restaurant in 2005 and never did I think I would still be in business in 2021!  Quality food with Great Service wins 'em over year after year. Hardest decision I've ever had to make is going on now - Sell It or Let my Niece take over operations. I personally am bored. So I've been training my niece for almost a full year and she is doing well.  I am going to take a 6 month sabbatical..... sort of...lol.  I will still be doing the accounting, payroll, taxes and such so that I can make sure she is staying profitable and on top of guest experiences.  If she keeps it running I will stay the course and get another job doing something exciting and new; if she gets bored or numbers start to fall I will have to step in and decide all over again if I am going to stay with it or sell it. I'm proud of my business longevity and I LOVE LOVE LOVE my guests!!  But there has to be something else I haven't conquered yet in my 49 years!! 😎

Message 8 of 67
Beta Member

Agree on the quality. Often time the difference from mediocre and delicious is a few bucks. Never buy the cheapest or most expensive item. The sweet spot and difference maker is in the middle.


Message 9 of 67

THe hardest decision ive had to make was if it was worth the suffering i experienced. The suffering pertains to the company not taking off. I had to figure out what was actually the problem and if the issue causing the company failure was fixable or if i had to just accept the loses. After looking into the issues it came down to myself not hiring the right people for what i requested from them. So due to improper hiring i caused no productivity. At that point i new i still had a chance at salvaging my business. So i cut back funds typically used on food and luxuries and put it all on the line. Im finally at the end of the downside and am glad i risked it because now i have a great appreciation for what i've created. This is just one scenario though and doesnt apply all the time. You have to know when to cut your losses. If you know it can work though never let people discourage you from your dreams of creating something special that you know will help people! I hope this helped. 


My favorite quote, "You can NEVER see new Beaches if you never leave the Shore"

Message 10 of 67

Firing dead weight.

Message 11 of 67

Hi Cranoia,  The best advice I ever received was from the person that appointed me to my first corporate management position.  He said "No breath is better than bad breath."  It may be painful to fire someone, but if they are not carrying their weight, if they are not doing the job, if they don't share your vision for customer service, the other employees know it and they are wondering what they have to do more work to cover for this person.  Overall, it creates a poor working environment at best and at worst it creates a toxic work environment with everyone from you, to employees, to customers paying the price for retaining one person with "bad breath."  Keep in mind, it doesn't mean this is a bad person - it just means they are a bad fit for this position or organization and they will have an opportunity to excel in another role or organization.

Terry Young
Message 12 of 67

So true, thanks I struggle with it, but you are so right, it created a toxic place for the other employees as they were all walking on eggshells. It had to be done, and I grew and learned from it. Thanks for the advice, I will remember those words on my next head chopping adventure.


Message 13 of 67
Beta Member

Laying off people to survive Covid slowdowns. We're in CA, which locked down pretty hard, and we do most of our sales at events and catering. None of that was happening. It was a clear decision, and we did survive, but it broke me inside and honestly I lost some love for my business that I haven't recovered.  
Message 14 of 67

I am in California too and my gift shop is in a flea market. We are open only Saturday/Sunday. The past year was bad. I was barely making the rent, and could not buy new inventory. I was extremely thankful that I was the sole employee and did not have to let go anyone. That would have broke me mentally. It is still hard but getting better slowly, ever so slowly.People are not quite ready to part with their hard earn money. Fear of what the future will bring really shocked everyone. Now, as an owner and decision maker, we are having another problem: Reeorders are very slow in coming. One cannot forget that the rest of the world is also hurt by COVID and they cannot supply us.  So my orders are very small, and I make a note to thank each suppliers and wish them good health. For the past 2 months, my orders have come in a bit faster.. So GeoffCJ, don't lose hope, and I wish you good health and happiness in your future events.

Message 15 of 67
Super Seller

@cgj2 Have you tried selling at farmers' markets, Here in LA a lot of them allow crafters (gift items, jewelry, etc) There are farmers' markets 7 days per week here in LA and numerous per day.


Life is too short to eat boring cheese.
Message 16 of 67

man 😕 CA was the worst- dont loose love for you business, lose faith in your govt. 

Message 17 of 67

To close a location during COVID. But was the smartest too. 

Message 18 of 67
Super Seller

In general, understanding the difference between an expense and an investment, and then take the leap on an investment.

Kamala Allison, Owner
In store: 1528 Pacific Ave, Santa Cruz, CA
Online: www.ShopFybr.com
Message 19 of 67

I think the hardest decision i have had to make was pricing. wanting to be reasonable but at the same time knowing my worth. it hard when i mean if pricing is too high your not going to get any customers and if its too low you will have alot of customers but you want be making enough money to actually run your business .

Message 20 of 67

The decision to close my business and start over. 


Based on some serious "look myself in the mirror time" I came to admit that I lacked the drive to do what was required for the business I had. I got a book The Five Minute Business Plan.  Next question - What am I willing to do? What are my strengths and most importantly weaknesses.


I discovered that paperwork and employees are problematic for me. So I designed a business that required neither. 

The decision I made was "I want all the business that I can do myself without any employees and minimal paperwork".


I am a chiropractor. My practice is on autopilot. No insurance, no paperwork to speak of. No accounts receivable. Just Square appointments and payments. It is a dream come true.  I am leaving on a 10 day vacation. lol






Message 21 of 67