The Emotional Journey of a Bootstrapped Founder: Fear of Disappointing Your Customers

Reading Time: 7 minutes

Over the last few weeks, you will have noticed that I have started talking more about the emotional impact of entrepreneurship. I talked about impostor syndrome, people cloning businesses, the loss and grief of selling a business, all topics that most people keep quiet about.

I remember keeping quiet about this myself a few years ago. I was in the middle of running the tech side of FeedbackPanda, and I was stretching myself thin. The thoughts in my mind developed a destructive feedback loop, and I experienced many doubts, a lot of stress, and intense anxiety.

For that reason, I started The Bootstrapped Founder blog, newsletter, and podcast in the first place. When we sold our business, I finally had time to deal with all that emotional baggage. Putting it on the page and sharing how I dealt with it during the wild ride of running and growing a business helped me find peace and meaning. It now allows me to help other founders become more aware of these very real problems.

I want to re-invigorate a series of articles that I wrote right after we sold FeedbackPanda. That series is called The Emotional Journey of a Bootstrapped Founder. In this series, I talk about how certain situations and incidents can evoke strong emotions and how to deal with them. I will explain how I reflected and reframed those thoughts and feelings. I will then suggest actions for immediate and long-term improvements.

Today, I want to tackle the Fear of Disappointing Your Customers.

I remember a particular situation from 2019 that I want to share here. Our browser integration broke overnight. We had a few thousand customers at that time. The moment the first customer reported this, I felt like I needed to fix and update the extension immediately.

So far, so normal. The problem is that I was right in the middle of a family birthday. We were at Danielle’s childhood home, and while the party was booming in the basement, I sat on Danielle’s bed, fixing the bug. Instead of spending the time with her loving family, I retreated to fix a piece of software that wouldn’t affect our customer for another ten hours.

In retrospect, leaving the rest of the family behind to deal with this little issue was unnecessary. This bug didn’t impact our customers’ ability to use our product; it was just a small nuisance. But back then, I felt strongly compelled to deal with it immediately. It was the middle of the night, and I could have waited until the morning to work on this.

Why did I feel like I would be letting down customers if I don’t act immediately? Would they really be so terribly disappointed if I didn’t spend every second of my day trying to stay on top of these things?

It turns out that this is a trick of our brain. It’s a myopic distortion of our perception to think that our product is a giant part of our customer’s world. In reality, it’s one of the hundreds, if not thousands little concerns that all compete for their attention. If your service has a little trouble for a few hours, they’ll likely take note, deal with their problem another way, and return to your product tomorrow. This is particularly likely when your customers understand that you’re a bootstrapped founder, dealing with these things yourself. The moment your customers are aware of your motivation to empower them, they will understand your predicament and be supportive — most of the time. There will always be people who have exhausted their capacity for patience, but generally, your customers are on your side, particularly if you have established a brand as a transparent founder by building your business in public.

The trust that you build by being there for your customers and sharing your journey translates into patience. Even though they have expectations, often high ones, your customers know that you will get to solving their problem eventually. The more you are understood to be a human being, the more patience they will show you.

That means that you have time to fix problems and build solutions carefully. I have built too many fixes for bugs introduced by other fixes caused by trying to resolve an issue too quickly. If you try to be too fast, you might create two non-optimal experiences for your customers instead of the one that you’re trying to respond to.

Errors and bugs are part of running a software business. People know that, and while this depends on the expectations that people have for your product’s overall quality, your service will still be usable unless your whole system is down. Unless it’s a catastrophic failure — which you should absolutely respond to immediately — your perception of the gravity of any bug will likely be much higher than what your customers think.

Here is a reframing opportunity for whenever you feel this fear of disappointing your customers: the opportunity of value-nurturing, for showing your customers what they actually have when things work well, is real. Of course, you don’t want to have this happen too often, but sometimes, this perceived disappointment is just a reflection of what your customers otherwise have access to at all times.

Here are a few things you can do to prepare for these moments to lessen the stress levels so you can make an intentional choice about how much effort to put into fixing this issue and if this really should be done immediately:

Prepare a Message for Your Customers. The moment you notice that something needs to be done, draft a short message that you can re-use to communicate this to your customers while you’re dealing with the situation.

We had such a situation when Firefox mistakenly disabled all addons for all their users. We had a couple hundred customers who used that browser and were not technical enough to understand the reasons for this glitch. They just were confused that their little panda icon was not there anymore. Here is what I did to make sure this would be something that I could adequately communicate during the rush hours of our user’s day:

  • I prepared a message explaining the situation, what was happening, and that we’re working on it.
  • I looked for a social media link by Mozilla, promising to fix this quickly, and added that to the message.
  • I tried to explain the issue but didn’t get technical. We couldn’t fix it, as it was a Mozilla issue, but our customers would still think it’s our fault. No need to shift blame. Own it, and promise to resolve.
  • Since Mozilla quickly tried to fix this issue, we had a time horizon to communicate to our customers. I made sure this was part of the message.

I make the message copy&paste-able, added it to our Intercom snippet collection, and used it whenever a customer would reach out. In this case, there wasn’t much to do, but if this is a problem that you can fix, having this message easily available will allow you to focus on the solution.

At best, you have someone else take over customer support while you deal with this issue. As a solopreneur, just write the message and have it in your clipboard, ready to be pasted into any conversation. Using a clipboard manager or tools like TextExpander will help significantly.

Here is a template that worked pretty well for us:

“Hello, thank you for reaching out about this. We have noticed that xzy is currently experiencing issues. I am working on a solution right now. The service will be restored within the next hour or two. I will keep you updated!”

Communicate immediately that you’re working on it, but don’t necessarily work on it immediately. Remember that only the critical issues should receive critical responses. Otherwise, your business and its demands will start taking over your life.

Once you are done, reach out to everyone you told that you’d update them through the customer service channels they reached out in. This makes them feel heard and appreciated, which might just cause them to become evangelists for your product after such a supposedly negative event.

Have Customer Communication in place. If you want to reach your customers quickly, you’ll need open channels. Setting up Intercom or an email list is imperative to having access to people quickly when you need it. That way, you can respond and alleviate concerns immediately, and you will get a glimpse of the scope of impact, particularly using real-time chat tools. You’ll see how many people are affected just from the number of messages you receive. At that point, you can inform very vocal customers, and if you give them a well-worded and insightful message, they can amplify your “working on it” signal into their communities.

Be careful with using Status Pages. While this is only expected for tools that are being used by engineers, having a status page for your service is something many founders consider. These tools are great for larger organizations but terrible for a bootstrapped founder. Offering a central status page creates incredibly high expectations with your customers. They will expect immediate updates whenever something happens because this is what happens when large software businesses have outages. They expect detailed error messages and reflections while you’re frantically searching for a solution to a technical issue.

Status pages are only ever used by technical customers. Your non-tech customers will reach out through Customer Service anyhow. Not only does this incur costs and engineering overhead, but it will also split your attention when dealing with your customers asking questions. Status pages are an expensive distraction: either you use a hosted solution that won’t be cheap or host it yourself only to have one more thing that might fail.

Take a minute to reflect on how much immediacy is needed. If your whole service ran into a wall and needs to be restarted, deal with it immediately. If a non-critical integration starts experiencing a few errors, you might not need to immediately drop out of a family birthday party.

You can do this methodically. Whenever you run into the feeling of disappointing your customers, make a note of how intensely you’re feeling this, solve the problem that causes this, then rate the true impact on a scale of one to ten after you had a few hours to breathe. Then, compare your notes. Over time, you will develop a sense of how your initial reaction differs from your less fear-driven perception.

What helped me calm myself down in these situations was remembering the non-impact the last little outage or bug had on our customers. The last time we ran into an issue, a few people complained out of hundreds, and they all were happy and joyful after we eventually resolved the issue. That usually caused me to deal with the problem confidently without freaking out about what people would think—because they think more positively about you and your business than you might think.

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