While I was working on answering questions for my upcoming Twitter audience-building course, I ran into this one: "What if it doesn't work?" While my immediate thoughts went to the random nature of eventual success and how only consistency will pave the way there, I soon arrived at a problem that lies much deeper than … Continue reading Fear-Setting
Category: Mental Health
Burnout
Every week, I see more people talking about burning out. It seems to be hitting anyone: from seasoned entrepreneurs with glowing track records to people scrapping their side projects because they can't even handle their day job anymore: people are struggling. I feel it too. Being cooped up for years isn't cool, not even for … Continue reading Burnout
What Founders Can Learn From the Facebook Outage
If Facebook can survive a 6-hour outage, so can you. Let's talk about unexpected downtime, which is often a direct consequence of dependency risk. Even Facebook experiences platform dependency risk. In fact, their attempt to avoid platform dependency risk introduced a new dependency, which caused this fail cascade to happen. Because Facebook truly wants to … Continue reading What Founders Can Learn From the Facebook Outage
The Creeping Nature of Stress for a SaaS Founder
I did an Ask-me-Anything on ProductHunt this week, and one question stood out to me. Jon Jackson asked me about the kind of life I led while running the business, how stressful it was, and what that looked like. Doing AmAs gives me a lot of opportunities to reflect on those things. Now that there … Continue reading The Creeping Nature of Stress for a SaaS Founder
Impostor Syndrome and Building Capital
There will be days when you feel like you have nothing to say. You might wonder why you should be the one talking about anything when there are people out there who are much more experienced than you. You feel like you're acting more knowledgeable than you truly are. I have been there. Even now, … Continue reading Impostor Syndrome and Building Capital
Accountability Systems for Founders
Some days, I don't feel like doing anything entrepreneurial at all. It's not that I'm burned out or disinterested, not at all. But there are those days where all I want to do is curl up on the couch and read a good book. Often, I take the day off and indulge in whatever distraction … Continue reading Accountability Systems for Founders
SaaS, Self-Talk, and Many Small Bets
I often find myself trapped in the stories I tell myself. This week, I switched out the payment system of my SaaS PermanentLink. This is a critical part of my business, so I expected the actual coding part to be a high-pressure activity. After all, if I mess up the account management logic, paying customers … Continue reading SaaS, Self-Talk, and Many Small Bets
The Emotional Journey of a Bootstrapped Founder: Fear of Disappointing Your Customers
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 … Continue reading The Emotional Journey of a Bootstrapped Founder: Fear of Disappointing Your Customers
Motivation Will Eventually Go Away: Build Accountability Systems Instead
Motivation is a powerful initial force. It provides momentum. When we start projects, we need that momentum to push us through the initial collision with reality when we learn of all the complex choices we have to make to get things off the ground. It's the motivation to learn, to discover, and to create that … Continue reading Motivation Will Eventually Go Away: Build Accountability Systems Instead
The Bootstrapper’s Plight: The Social Headaches of Building a Business
Many founders choose to create a lifestyle business. They have read the 4-Hour-Workweek by Tim Ferriss and now want to build a company that can sustain a life of travel, enjoying the world, and spending time with their loved ones. Gone will be the days of overtime, the excruciating commutes, the pointless teambuilding weekends. Well, … Continue reading The Bootstrapper’s Plight: The Social Headaches of Building a Business
