A friend recently approached me, asking how he could overcome a feeling of paralysis. He felt stuck figuring out what the next steps are in getting his product out and front of customers.

I can very much relate to that feeling, it’s been a continuous companion over the last 3+ years in building out Travis CI. While I didn’t have any good advice, I had a few stories of my own to share.

In 2012 I was working on our billing app. It didn't feel that important, but when you think about it, it's kind of an important piece of making money for a SaaS product.

I felt continuously stuck and afraid to finish it up, paralyzed by the fear that it would break and that it wouldn't work for weird reasons. In some ways I felt like I over-engineered it, just to make sure it's resilient enough to all the weird stuff that happens with payment systems.

Finishing it up and bringing it to a state where I could confidently say "Let's do this!" took me the better of two months. While we weren't sure if the product is stable enough (it wasn't) to justify charging for it, we tried to do it anyway, and we went into a private beta for months. We made it a paid one, a generally unheard-of concept in a world where beta usually means free, or where services remain in perpetual beta state.

A similar thing happened when we decided on and published our pricing, which was deliberately higher than that of our competition, and there were public complaints about it. We were still confident, but that kind of negative feedback hampered us. We got over that hill in the end, and decided on just pushing through with the pricing and see where it leads us.

The next time this happened was when we were faced with the question of how long we want our private beta to continue. We were in private beta for almost a year, which is ridiculous in hindsight. There were so many things we were worried about, mostly regarding capacity and not being able to support the onslaught of customers, it kept us from making the call. In the end, getting our of private beta and opening up the product to everyone gave us a huge spurt in new customers, and from thereon out we saw organic and steady growth.

When you step into unknown territory, the paralysis is a natural thing to happen. When you don't know what's going to happen, the simplest thing for us is to stay away from taking the plunge. I know this feeling very well, and I'm finding myself faced with it again right now. It gets even harder when it stops just being you, and when other people’s income and supporting their families is on the line.

What I found to be useful in those situations is to think about what it is that I'm really afraid of, what's the worst that could happen in the situation I feel so paralyzed by.

Is the worst part that no one's going to give us money? Is the worst part that the billing system might fail and people can't give us money? Is the worst that we’ll have some unhappy customers, or an unhappy team?

Thinking about that nudges yourself to think about your fear and your paralysis, and to think about what you’re really afraid of rather than just feeling stuck by the fear itself.

The fear of failure and the accompanying paralysis seeps through all aspects of your business. When it’s not about the billing system, it’s about where to go with the product, figuring out what to do next. The product will never be finished, it will never be good enough for you, in particular for you who've invested so much into it. This alone can lead you to a perpetual state of not being able to move when move is the very thing you have to do.

Channeled right, this can be a powerful driver and motivation. But it can also be a constant feeling of not achieving everything you want to achieve. For this situation, the simplest thing you can ask yourself is: what's the simplest thing I can add and ship for this to be (more) useful and valuable to someone? It's not a definition of finished, but it's a definition of good enough.

If you can find a few folks to give you money for that, then you're on a great path, and it’s the most powerful motivator from hereon out. Can you get 10 customers to give you money? Can you get 100? 1000?

That's the moment where you'll end up feeling silly about your paralysis. That moment when your first customer, your first ten customers, give you their credit card and their money, that's the best moment. It's not a guarantee what you've built is going to be successful in the long run, but it's incredibly validating and motivating for you to push on.

The bad news is that the feeling of paralysis is probably never going to go away. As your business grows, you’ll continuously be faced with new decisions whose outcome you cannot foresee.

What you will get better at is getting a grasp of what you’re really afraid of and, most importantly, at recovering from when things go wrong. You’ll be more resilient to these failures over time, and you’ll find ways to pick yourself up again and move on, learning as you go. The truth is that you’re not alone in this fear and paralysis. It happens to a lot of people in similar situations.

One of the best ways to figure out how to get over it is to find people who are or have been in similar situations as you are now. Ask them how they felt, ask them what they did to get out of the paralysis, and find comfort in the fact that you’re not alone. If you ever feel like you need someone to chat to, feel free to reach out.

I've recently listened to a podcast on the topic of fear and founders, I'd recommend you listen to it and think about how it applies to you.

About a year ago I met one of our team members in person for the first time. We hung out for the entire day, talking about all kinds of things, problems we were facing with our company at the time were amongst them.

During those conversations he taught me a simple yet rather powerful conversation technique: the awkward pause. It’s since become an important tool for me in 1:1s and conversations with other people.

When you talk about a problematic topic, there tends to be that moment when the other party stops talking. It can happen for lots of reasons. They don’t want to rat someone out, they don’t want to vent, they’re looking for the right words to express themselves, or the topic is so uncomfortable that they don’t want to continue talking about it.

When you’re impatient, it’s tempting to pick up the conversation in those moments. You ask further questions, you start talking about your point of view, you possibly even change the topic thinking that there’s not much more to get out of it.

Our intuition makes the awkward pause weird for both of us. It feels uncomfortable because no one is talking when this entire meeting is about talking, exchanging ideas and thoughts. The temptation to chime in and take over the conversation is big. Nobody likes the awkward pause.

When you chime in and interrupt the awkward pause, breaking this uncomfortable silence, the topic likely drops off the other person’s mind. Whatever troubles they’ve had, they’re unlikely to come up again in this meeting. They’re more likely to come up in some future conversation, when that person has gotten to a point where the topic has made them so unhappy that it turns into a vent, or maybe even in their resignation.

Interrupting the awkward pause means losing out on invaluable information and insight. What comes after the awkward pause is usually the real issues on that person’s mind. Whether what you’re going to hear is actionable or not, a vent, a personal issue, it’s the underlying issue of everything else you’ve talked about up until this point.

It’s the essence of what the conversation is all about. Breaking out of the awkward pause makes sure that essence is lost forever, possibly never to be seen again.

When you find yourself in a conversation and you can feel that you’re in an awkward pause moment, take a deep breath, focus on the other person and just wait. Resist the urge to continue the conversation and let the other person continue digging up the real issue that’s on their mind. Resist the urge to break out of the awkwardness and just let the other person talk when they’re ready.

Embracing the awkward pause is possibly one of the simplest and most effective tools to make you a better listener. It helps you build trust and develop more patience in conversations with your reports and your peers. I’d go as far as considering it an essential leadership skill.

Thanks, Dan, for teaching me an invaluable skill!

Tags: leadership

Being an introverted person in a leadership position is challenging. The one thing that exhaust you the most is now your main focus, interacting with people.

Personally, I didn’t fully realize that I have introverted tendencies until I read the book “Quiet: The Power of Introverts in a World That Can't Stop Talking”. I’d considered myself shy before then, feeling awkward trying to strike up smalltalk conversations, even just talking to other people, and constantly feeling a need to hide in quiet places to get away from chatter and to focus on my own thoughts.

I chalked it all up to being shy, and it left me in an uncomfortable position. Am I confident enough that I can pull out the relevant skills to be the CEO of an entire company, especially the people part?

Since then, I identified a few routines that helped me balance the needs of being in a leadership position with my introverted nature.

Read every day

Reading has become a very important part of my day and my progression from trying to get a startup off the ground to taking on the role of leading said startup as it matured.

Books have played an important part in helping me shape my own thinking about what I’d like our company to be, and about what I’d like to become. They’ve helped me narrow down on a few problems and helped me focus on solutions for them.

Beyond that, taking time to read is also time to reflect. A lot of books I’ve read have given me one or two key realizations about what I need to improve, what I’m doing well, and what our company can do differently. That one spark is worth reading an entire book for me.

For the introvert in me, reading is quiet time. I usually read first thing in the day, before I do anything else, and before the noise of the day starts crowding my mind, distracting it from the focus required to read.

Take long walks

I started taking walks after I read “Thinking, Fast & Slow”, which was a revelatory book for me, in terms of understanding myself, our customers and my team. Did I mention that reading is amazing, and that you should read every day?

Throughout the day, your brain is busy processing information, impressions, conversations, and adding to that, you’re trying to get it to focus on the work that needs to get done. Giving into this feeling of constant busyness is a downward spiral, leading to even more work, feeling stressed out, and emotionally exhausted.

For me, this ends up with work trickling into my personal life, be it by keeping my mind busy with work topics when I get home or on weekends, or affecting my moods at home.

Beyond reading, the best medium I’ve found to let those thoughts loose is to go on walks. Not just 20 minutes walks, but up to an hour. I walk at a relaxes speed and without any particular place in mind that I want to go. When you walk towards something, your mind is focused on that, and it doesn’t free up mental capacity to think and process. When you walk too fast, you may notice similar things.

I prefer to walk on familiar paths, a sort of roundtrip through the neighborhood, if you will.

After a while, magic happens. My head stops being overly busy, all those thoughts quiet down, and it feels like my head is a lot more responsive to giving it small triggers, like “I wonder what I could write about next?”, or much broader than that, “Containers?” Even small triggers suddenly leave my mind to wander around the topic, looking at different angles, maybe even finding a conclusion. It feels like magic.

Walking, all by myself, has turned out to be an important tool in processing information collected throughout the day, week and month, and working on extracting the patterns, the bigger picture, and what I could do about them.

Schedule time away from the office

As a leader, it’s likely you have a strong urge to always be around your team, being ready to jump in and help them at any time. You may also experience the fear of missing out, always wondering and curious what’s going on in your team, in team chat, and around the company.

That fear and the constant hovering adds to the emotional drain, contributing to a constant feeling of burnout, yet you feel guilty about not being there when your team needs you. It’s too hard to disconnect and focus on yourself and your own work, so that starts slipping and adds more to the constant state of busyness.

The above scenario isn’t an introvert’s problem, it’s the disease that our modern work day has become. In addition to feeling like I’m not progressing on my own work, this situation added to my own feeling of work topics trickling into my personal life, as little time was left to process all that information and recharge.

I started scheduling in weekly time away from the office, time that I spend in a coffee shop or elsewhere, noise-canceling headphones plugged in, working on bigger topics or just letting my mind wonder.

Initially, this didn’t feel like work, and I felt guilty, even selfish, for taking this time. But then I realized that I’m actually getting results from this time away from the office. It allows me to progress on important and bigger company topics, yet it gave me the isolated space that my introverted self needs to focus.

Taking walks, reading and spending time away from the office have become important stop gaps for me. They give me the time and space to process, recharge, figure out the bigger picture and come up with solutions for problems a crowded brain might not otherwise be able to extract.

Write every day

I sometimes struggle forming thoughts into concrete sentences when I talk to people. Part of that is because I’m having trouble forming a complete picture in my head, which I feel I need before I can say something. This reflects in how I approach thinking about bigger company topics as well. I need time and space to form my own opinions on things, and there is one tool that’s been the greatest help for me in this, writing.

I try to write, every day. Whether it’s working on a blog post, whether it’s writing an internal proposal, a summary of a call I’ve just had with someone to send around to the team, or simply writing a journal.

I’ve done the latter every day for almost two years now, and it’s become an essential part of my every day work. I’m using Day One whose reminders pop up multiple times throughout the day to help me capture what I’m thinking. Longer prose also goes into Day One at times, as some situations warrant a longer thought process, which is effectively reflected in what I write. For anything else, I’ve started trying out Ulysses, before I’ve used NValt and Byword for writing. I enjoy the simplicity of a full screen app with just a cursor.

It doesn’t really matter what tool you’re using, what matters is that you get beyond that moment of utter fear instilled by a blank screen with a blinking cursor on it and just write down what’s on your mind.

Writing requires me to focus, and it allows me to make sense of all the noise in my head. It’s my one outlet of processing all the information I collect, consciously or not, throughout the day.

Take your time in making decisions, but follow up on them

I need time to process information, to figure out any patterns and to come to my own conclusion on it. That process can involve writing, thinking, walking or listening to more opinions, gathering more insight from our diverse team.

That can sometimes be frustrating for others, especially when they want to move forward with something quickly. There are situations where I can just say “Sounds good.” and trust them with all my heart.

In other situations, I make a commitment to get back to them in a certain amount of time. The more you define that amount of time and keep your commitment, the more trust you can build with people over time. When they know that you do follow up and keep your own commitments, they’ll get more used to this being your mode of making decisions.

I found those two to be a good balance between making sure things don’t get stalled all the time and my own need for thinking things through a bit longer before I can come to a conclusion.

Beyond reading, writing, walking and spending time at the office, I’ve started meditating daily to try and tackle another issue I’ve mentioned earlier. Oftentimes I find my mind thinking about work things when I’m at home. I get distracted playing with my daughter, reading a book to her or over dinner, and I have an immediate urge to work on the thing I just thought about. I found that rather frustrating, and I’ve noticed that meditation helps me focus a lot more on the moment rather than have my mind wander endlessly.

What helps you foster your introverted nature as a leader? What helps you lead introverted people on your team? I’d love to hear about your experiences.