5 Business Lessons I Learned the Hard Way

After over 30 years in business, I have learned many lessons about business, sometimes the hard way. There’s a side of the story of business you don’t often see on LinkedIn or Instagram: the hard challenges that don’t have a magical fix. There are challenges that have solutions and plans that work, but they just aren’t as… Instagramable. They aren’t brimming with sage wisdom. These kinds of solutions are more mundane. They work so well that there is no need for a 3-act story to convince people to try them.

Across the highs and the lows of my businesses, both past and present, there are a few things I’ve learned that are taken for granted by other people in business. When facing systemic economic uncertainty, the wrong side of profit-and-loss statements, or the realization that a final hail Mary play still didn’t work out, it can be hard to take a step back and consider your next move. I know, I’ve been there, like many of you.

And while some disasters have been thankfully long since forgotten, there are five business lessons I’ve pulled from them that continue to be useful to me every day. This post isn’t about motivating you with the comeback story of the decade. This isn’t the inspirational LinkedIn post you may think it is. This post is for the tough, mundane decisions you make for your business every day. 

These are my five business lessons I learned the hard way.

#1. Everything is figure-out-able.

Ok, so maybe figure-out-able isn’t the most elegant way to say it, but it captures this point well. Let me say this right from the beginning: what I don’t mean here is that there are no fatal mistakes in business. There certainly are. What I mean here is that if you want to surmount a difficult challenge, the solution might just currently be beyond your capabilities. To figure it out, you will need to find resources to help you.

I can tell you from experience all about knowing that I didn’t have the knowledge to complete the job I needed to complete. I have moved from managing one restaurant location with a staff of 25 to managing seven restaurant locations across two restaurant franchises, administering HR and payroll for over 400 employees, maintaining and installing IT over multiple systems and computer networks, marketing for ten restaurants, and overseeing the construction of four new restaurants from the ground up. I’d be lying if I told you that I knew what I was doing every step of the way.

But every time I took on a project beyond my job duties, I learned that everything that challenged me can be figured out. Most things in business involve basic math, treating people with decency, and a lot of Google searches. The key is to have access to people with subject expertise and ask them a lot of questions, in addition to doing enough research that you could explain it to someone else. 

That actually brings me to my second lesson.

#2. Ask questions.

Often when I make a poor decision, it’s typically because I didn’t ask enough questions. Sometimes I’ve assumed someone knew all the facts of a situation when they did not. Other times I assumed I knew what they would say and so I didn’t ask anything. Don’t be afraid to ask questions and repeat the answer back to them to ensure everyone is on the same page.

I’ve learned to especially challenge someone's answer when it resembles, “because that’s how we always do it,” to one of my other questions. This is very common in my construction experience. (Yes, it is just as silly to write out ‘my construction experience’ as a restauranteur as it is to read it! But that’s kind of my point with this blog post.) There are thousands of details in construction plans, leaving hundreds of opportunities for error, or at the very least misinterpretation. Only by staying close to the construction when it was being done was I able to find the errors before it was too late.

In Human Resources, the stakes can be even higher.  Often I have to ask questions regarding if something is advisable or even legal. Connecting myself with a superior insurance broker with access to a current database of HR materials has been very helpful.  The information is definitely out there… you just need to know who to ask.

For my technical work with the restaurants’ software and hardware, I may not be able to set up a computer network from scratch, but I understand all the components, what they do, basic wiring diagrams, and can diagnose the problem when it crashes, thanks to picking the brains of the various help desk representatives.

Understanding the parts of complex systems is the third lesson I want to share with you.

#3. Large, difficult projects should be broken down into small steps.

Large projects can be overwhelming. Especially when it’s your first time doing something. I have found that by breaking the project into small steps and focusing on the next step at hand, I can progress my way through the project incrementally.

For example, when I had the idea of establishing a central location to answer the phones for seven restaurants, I had never heard or been inside such a place. But the concept made sense in our situation. And so our call center was born.

So first, I had to figure out how to make a phone ring in the call center and in the store simultaneously. Then, I asked myself: how the heck do I connect a remote computer in the call center to the computer network in the store? That took some work. Then, I learned how it was possible to take an order in the call center and make the order print up in the correct store from which the customer wanted to pick it up. Needless to say, it took a while!

At each step, I had no idea if this would work technically or would work as a business solution. I simply focused on the next task. Now the call center services seven locations, achieving a higher quality of customer service, and saving a little on payroll. Unexpectedly, it was a life-saver during COVID when we were operating on drastically reduced staff in the stores.

This kind of project analysis required keeping track of many moving parts simultaneously. Hence, my next lesson is to focus on your organizational skills.

#4. Stay organized.

In the business world, you will be pulled in multiple directions at the same time. You will never remember everything that needs to be done if you don’t continuously add to your to-do list. I have found the most effective method to track it all is using a notes app on my phone. (I personally use Google Keep.) It allows me to check off things as I complete them and add more items as they come up. I maintain multiple lists, including High Priority Long Term Projects, a George Supply list, and links to various things I want to come back to on internet searches.

If you’re interested in how to use your phone’s own pre-installed note-taking app as an easy and free way of keeping track of your projects, I wrote about that elsewhere on the Business for Makers Blog.

I make a concerted effort to get the high priority work list as close to cleared on Friday as possible, so I can focus on the George Supply list over the weekend. This is key for making my system work. It’s not enough to just collect to-do lists. You will need to work actively to check them off your list, too!

I know that is easier said than done, though. Sometimes things fall through the cracks. That’s actually my last lesson.

#5: You will never be perfect

Perfection is elusive. If you aim for perfection, you may never finish a project. Rather than measuring your projects or your business against the idea of perfection, it is far more realistic to focus on your progress towards competency and expertise. How much closer to expertise are you than you were a week ago, a month ago, or a year ago? Consistent progress is better than perfection.

Most new small businesses make a product that is less than perfect. But knowing that only through repetition will they see improvement, they must soldier on. That product may never become perfect, but it will get a heck of a lot better with hard work. And that’s what people will pay money for: a great product over a good product.

In Summary

So many aspects of operating a business can be scary and overwhelming. Especially in subject areas you are unfamiliar with. The key is to realize everything can be figured out, if you ask enough questions from experts, break projects down into small pieces to be accomplished, and stay organized. These will give you the confidence to move forward. 

These are the everyday skills and lessons that have helped me as my business has evolved and grown. Like I said at the beginning: they are not revolutionary. But they are mundane enough to be taken for granted by too many people. In my experience, however, they are the keys to a successful business.

I’m excited to watch your own business grow, as well! Let me know about the everyday decisions that you make that help your business!

Have questions about building your maker brand and business? Subscribe to the Business for Makers Blog and Business for Makers Podcast for insights and tips. Tune to Sawdust Talk on IGTV Live on Wednesdays at 10 pm CST to hear from makers about their projects and business and meet some great members of the maker community.

Check out georgesupplyco.com for more resources for growing your maker business!



Scott Chervitz is owner of George Supply Company, dedicated to helping woodshops build their brand. See more at GeorgeSupplyCo.com. You can reach him at Scott@GeorgeSupplyCo.com, on Instagram at @GeorgeSupplyCompany or Twitter @ScottChervitz

Brian Chervitz M.S. is Associate Instructional Designer at the University of Wisconsin Extended Campus.

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