Navigating Success and Failure: You’re Human, and That’s Okay

When you run a business, there are constant ups and downs of successes and failures. Everything can go exactly according to plan and be an immediate success, or disaster after disaster can hit and throw away all of the work you did. 


It can be difficult to maintain motivation through the ups and downs of running a business. Business-owner burnout is real and can happen when we get discouraged from feeling like things only go wrong. How can you prevent getting disheartened and keep up your motivation


Let’s dive into strategies that I learned as business owner to celebrate the wins, to learn from the mistakes, and to cut yourself a whole lot of slack when things don’t go perfectly. You’re human, and that’s okay.




Celebrate the wins


When your business does well, it’s really important to take the time to celebrate the wins. If you close a huge deal, reach a major milestone, increase profit year over year, or otherwise make a small or big win in your business, you should absolutely take some time to bask in it. Enjoy it! 


Find ways to inject some fun into things to keep up motivation and celebrate. Whether it’s by taking some time off, by treating yourself to something special, by holding a little party for your team, or by taking a moment to relax, find what works for you.


For small wins I love to take an extra day off in the middle of the week to relax and enjoy myself in a low-stress way. I tend to go to a good park to take a nice walk; to sit in a local cafe or a Starbucks for a few hours to read a book and sip on a fancy drink, and maybe to get a nice dessert from this French bakery in my neighborhood. For bigger wins I love to treat myself to a longer trip to a new city or country.


Rushing back to the grind after a big win is exhausting. If you rush from one win to chasing the next milestone, you can quickly find yourself on the path to burnout. The wins can start to lose meaning, and you can lose your motivation. If you don’t recognize and enjoy them, wins aren’t really wins. They’re just another day. 


Even if the successes aren’t solely because of you, you can still celebrate and enjoy them. Just take the time to understand how they happened. 



©Disney on Facebook.©Disney on Facebook.


Learn from losses


Just as important as it is to celebrate when things go well, it’s important to recognize and learn from the mistakes when things go wrong. Failure isn’t necessarily a bad thing. When things don’t go the way we expect, there’s usually a lesson that can highlight a way to improve.


For most of my life, my dad and I owned and ran an ice cream shop together. When the pandemic hit, we had to make some wide, sweeping adjustments to how we ran things. We prioritized the safety of our employees by serving out of our pickup window rather than letting customers into our store, and we packed up every order in bags. Some of our customers weren’t the happiest about that, and our sales definitely dropped due to the inconvenience. 


Ever since the customer backlash from that choice I made, I became pretty terrified any time it was up to me to make big decisions that could drastically change our business. I worried constantly that I would completely mess up the business with any choice that I made, that it might upset our customers and cause irreparable harm. Since I was the one making the decisions, I felt a lot of pressure on myself. 


I know that my dad wouldn’t have held it against me if the choices didn’t work out, especially since we would always talk through the pros and cons of each of them before we moved forward. Still I had a lot of anxiety about it. I was worried that, in time, I might freeze up and not be able to follow through with any decisions or changes at all. 


But when you run a business, decisions need to be made. Staying still and not making choices can do more harm than making bad calls. You never know the impact your decisions will have, but that can’t stop you from doing what you can to run your business how you think is best. 


My dad really helped with that. If I made a decision that didn’t work out and got upset, he would immediately brush it off and encourage me to do the same.


We tried something and it didn’t work, so we kept moving. We would do what we could to remedy it, change things back or try something else. We would apologize to our customers or employees as needed, own our mistakes, and keep going. 


You really do have to brush off the failures and not dwell on your mistakes. Almost nothing is irreversible. You can basically always come back from anything if you work hard enough. 


It’s not your fault if things don’t go well, as long as you went into it with good intentions, due diligence, and out of a good place. Let the bad slide off, learn the lessons that you can, and move on to run the business for another day. 



Take it easy on yourself and give yourself grace. @Pesso 






Create your own definition of success


There are a lot of different ways to succeed and grow, both for the business and for the owner. Some people look at profit, unit sales, number of transactions, or number of customers. While those are all great ways to measure the success of your business, they can all be far out of your control.


I like to focus on the impact on real people. A business owner can make a few big sales, or it can make a single customer’s day better. A business can expand into a second location, or it can deepen relationships with the local community. Fulfilling acts like these can be incredibly impactful for you and your business, and they are another way to be truly successful. 


The best part is that these are all completely within your power to achieve at any time. You can surprise and delight a customer with a smile and a warm welcome, or by adding a free extra to their order. You can send an email to a local organization to offer a donation or to sponsor their next event. 


If you start to think about success in ways you can control, you can make sure you earn that sense of accomplishment and stay motivated to keep running your business. 



Look ahead


You’re working hard to run your business, and you deserve to give yourself a lot of credit for that. It’s so important to keep the good and the bad in perspective. Things will always go wrong, but it’s up to you to decide how to handle it and what you do next. Enjoy the good, move through the bad, and stay excited about all of the things you can contribute and accomplish tomorrow.


Now, I’d love to hear from you. What have you learned from business mistakes or failures? And, how do you celebrate your successes?

Aylon Pesso is the Square Small Business Evangelist, helping sellers run their businesses better. Based in the U.S., he is a former small-business owner, consultant, and Square seller.


This article is only for informational purposes. The information provided in this article solely reflects the speakers’ views and are not endorsed by Square. This article is limited in scope and is only intended as a high-level overview of the topics mentioned.

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