Start Up

Fail to Succeed

I’m a failure. There, I said it. I have a secret though. The secret is that we’re all failures. No matter what is on your socials, what life you put out to the world. We are all failures. We try to speak long before we’re successful. We fall hundreds of times before we walk. The trick is how we get back up. We like to think that once we get past childhood, once we’re “grown up” we don’t fail anymore. We all know exactly what we’re doing and we know how to function in our jobs, in our lives. We make jokes about “adulting”, only admitting to our insecurities through a veil of humor. Why do we think that when we’re adults we stop learning, stop failing?

I’ve heard from a lot of people that they’re “lifelong learners’. They want to learn something every day, big or small. The only way we really learn something is to try it, fail, and try with more information the next time. Running a business means facing failure head on, learning from it, and knowing that you’ll make it through.

My first big failure was a few years into my business. Sales had been doubling every year for a few years, which was fantastic. I had hired some help which was going well. But I had a problem. My billing system had never been elaborate. I charged for 10 walks at a time. When the punch card was filled up, I asked them to pay me again. This was easy enough when it was just me but with other dog walkers there were clients I wasn’t seeing. The system no longer worked. I spent months researching a solution and in that time I lost literally thousands of dollars. I was paying my dog walkers but I wasn’t getting paid for the walks they were doing. I didn’t know what to do. I didn’t want to change everyone over to something else that wouldn’t work. I was beyond stressed and my credit card debt was going up and up. I decided on something, and it didn’t work. I spent months and more money only to discover that it just wouldn’t work for us. I finally found a solution that did work but all told, I was losing money for about a year. By the end of it, I was paying $500 a month in credit card interest and I was lost. How was I ever going to pull myself out of this hole? Was this the end? What had I done?

As clients began paying their bills, things got better but I still wasn’t really making any headway on my debt. I tried to get a loan to drop the interest rates and consolidate it but I couldn’t. I was beyond stressed. I needed help. I called my aunt, who listened, asked if I wanted help and then jumped in with both feet. She went through every charge with me and gave me small tasks to do to start seeing the light. I will be forever grateful to her for that. I would not be where I am without her.

You’re probably thinking, well that’s great but she’s not my aunt so what the heck am I supposed to do with this? And it’s a good question. I probably can’t tell you how to get out of your specific problem in a blog post. What I can do is help you reframe your perspective. There could be any number of challenges standing in your way right now. The first thing I like to do is write them down, like they’re a to do list. Like Dumbledore and his pensieve, getting the thoughts out of your head gives you new perspective. Framing them like a to do list helps you prepare to tackle them. Some of the challenge here comes in how you word your obstacles. For example, one challenge could be: I’m broke. That feels like a hard thing to overcome but if you say: I don’t have enough money or I need more money. There’s a really obvious solution to that. If you’re a small business owner, maybe it’s as simple as raising your prices. You might need to get more clients, or streamline your processes and drop your expenses. Now you have direction. You can break that down into an actual to do list.

Here’s an example:

Challenges:

Need more money

Need more time

Want better company culture

To Do List:

Evaluate processes and streamline where possible

Research cheaper sources for supplies or call current suppliers and ask about bulk/prepay discounts etc

Evaluate if raising the prices is feasible

Survey staff about what they’d want to see for culture.

Create the culture you and your staff want (this is going to end up being another to do list)

Schedule some time off a month from now. You only get it if you’ve made progress on the list.


We started with: I don’t have enough money or time and I don’t know how to get it and I need to pay my bills and ahhhhhhh. It’s scary and overwhelming. Once we write it down though, the answers often make themselves apparent. Of course we all know that to make more money we need more clients but sometimes laying it out and making a plan is all you really need. Realistically, you might not be able to do all the things on that list by yourself. If you sell goods, ask your production manager what they think about cutting costs. Get the cold hard numbers. Figure out what you’re making on each item. You can hire someone to do this for you (I know, more money going out the door but I promise it’s worth it if you don’t know how to do it yourself). Talking to your staff about their ideas will also encourage a good culture. People like to be heard and often have ideas that would have never even occurred to you. Have a contest to make the best pitch for a new product. There are all kinds of things you can do here. All of these things will promote a better company culture and of course happy employees means less turnover which means...more money.


More time can be tricky but giving yourself a reward gives you a motivation to keep going. It doesn’t need to be a big expensive vacation. You might just take a weekend off and spend it with your family. Drive up to the mountains or out to the beach and take some time for yourself. You might even just get to watch the whole football or baseball game or whatever on TV, uninterrupted. Make sure someone can cover for you, you have a month to plan. When I didn’t have staff I would hand my phone to a friend and ask them to keep an eye on it. Give yourself clear goals to achieve your time off. You can continue breaking down your to do list from here so maybe you need to complete 5 steps out of 10 on each item. Whatever makes sense to you.

It’s true you don’t have my aunt, but you probably have someone who can help you work through this. Let them read over your list and help you make a plan. They don’t need to be experts but they do need to know you and to be willing to help you.


Share some of your to do lists! I’d love to see them. Next week we’ll talk about Analysis Paralysis.