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How's it been? Has it been good? I'm glad to hear it. It's been really great for me to be here. I've enjoyed this so much.
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I'm so thankful to meet many of you. There are still many more that I have not met. I can be really shy, but I'd love to meet all of you.
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So if I don't come talk to you, please come talk to me if you'd like. I would love to chat. I'm always looking to meet more Rubyists, and I just love this community. So, thanks.
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Today's talk is the last one here. Welcome to "Making it as an Indie Developer: Secrets of the Fire Swamp."
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When I was a teenager growing up in the 90s, this was my favorite movie. I think I had the entire script memorized at one point.
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It's embedded pretty deeply in my brain, and there are parts of this movie that still spring to mind decades later. Here's one of those parts: Wesley and Buttercup are being chased by the evil Prince Humperdinck. To avoid capture, they enter the Fire Swamp, a dangerous forest that almost everyone avoids.
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There, they encounter the three terrors of the Fire Swamp: the flame spurt, the lightning sand, and the ROUSes, the Rodents of Unusual Size. They manage to survive each one and emerge on the far side of the forest.
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Suddenly, they are surprised by Prince Humperdinck and his men. Humperdinck commands them to surrender, but then Wesley replies, "Ah, but how will you capture us? We know the secrets of the Fire Swamp. We can live there quite happily."
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I've thought about this scene quite often over the years. It's become a personal metaphor for how gaining knowledge and building risk tolerance can grant you access, and even a degree of safety and comfort, in a place most people would consider unlivable.
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In that place, you may discover a new kind of freedom - freedom from the defaults or conventions found on the outside. Working for yourself is a little bit like the Fire Swamp. It's unpredictable; it can be dangerous, and most people avoid it.
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However, I would like to propose that if you can learn the secrets, get comfortable with the risk, and protect your downside, you can live there quite happily for some time.
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Please know, I'm not suggesting that every employer is Prince Humperdinck trying to make you suffer in the Pit of Despair, though I can empathize if you feel that way.
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Instead, I'm trying to suggest that traditional employment is a default we sometimes accept because the Fire Swamp seems unlivable.
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What I want to convince you of today is simply that it is livable. I'm not saying you have to leave your full-time job if you have one that you love, but rather that the Fire Swamp could be a reasonable option for you once you learn its secrets.
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So, if you are an indie developer already, you may be well ahead of me, but I'm hoping that you come away from this talk with insight for a challenge you're facing or a new idea to inspire you.
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If you are curious and considering the indie path, I want to lay out a framework for uncovering and managing the unknowns of working on your own. And if you're happily employed, I want to offer you a reasonable backup plan just in case something in your life or work changes.
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Hello, I'm Jeremy Smith. I'm a designer and developer, and I run a tiny one-person web studio specializing in Rails application development, currently serving solo founders with SaaS products.
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I've been working on my own since 2013, and I live in Greenville, South Carolina, in the eastern part of the U.S., with my family: my wife, Christy, and our three kids, ages 17, 15, and 11.
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I'm also the co-host of the IndieRails podcast with my good friend Jess Brown. Here's a recent interview with Adam McCrae of Judo Scale, or as you may know it, Rails Auto Scale.
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I'm the lead organizer for Blue Ridge Ruby, a new Ruby conference that was held back in June in the mountains of North Carolina.
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Now, you may still be wondering why you should listen to me. Let me also tell you what I'm not.
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I'm not a 10x developer. I've been building web applications for about 20 years, but I would guess I'm a pretty average senior-level developer.
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I'm not a high-energy, high-output person. It's taken me a long time to realize it, but I'm not one of them.
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I can't grind it out at a full-time job, work on a side project or venture, and then still take care of myself and my family.
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Also, I'm not a big risk-taker. I have had lots of dreams and schemes, but I don't have a naturally high risk tolerance.
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I get stressed out easily and often doubt myself. Despite that, I've managed to make it on my own for 10 years.
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I exercise a great amount of control over when and where I work. I take a more active role in choosing projects and clients and pursue several personal and professional goals.
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These might have been difficult or impossible for me with a regular full-time job.
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For example, when our kids were little, I helped my wife homeschool them. I attended Urban Farm School for three days a week for seven months while doing client work part-time on the side.
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I built an online video platform to teach people agriculture and homesteading skills and helped produce several video courses that we sold.
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I took our family on several long cross-country trips during the summers, which is hard to do with a standard two-week vacation in the U.S.
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As I mentioned, I've organized a Ruby conference for the first time this year. Thank you.
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None of these accomplishments may be interesting or impressive to you, but I hope they at least show you that taking the indie path can allow ordinary developers to pursue dreams.
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Now, I want to lay out a framework for making it as an indie developer. These are the secrets of the Fire Swamp. Knowing and preparing well for these can help you avoid ruinous surprises.
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I say 'making it' intentionally and not 'crushing it' or 'killing it' because the goal, first and foremost, is simply to make it, to not fail, to protect your downside, and to survive.
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I learned this framing recently from Daniel Vassallo in his course on small bets. Daniel is well-known for quitting his high-paying job as a software engineer at Amazon to work for himself.
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He says when you move from regular employment to self-employment, you enter an unpredictable world, and your tactics for operating in that world have to be different.
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The goal is to focus on survival and avoid a 'game over' scenario.
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So here are the keys: knowing your why, making the transition, managing yourself, finding customers, and thinking like a business.
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Let's start with knowing your why. When I was in my late 20s, I dreamed of buying and renovating a fixer-upper.
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My wife and I bought this 100-year-old rundown house in a historic Cotton Mill Village.
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100 years may not seem old in Europe, but it's ancient by U.S. standards. We had just had our second child, and it was late 2008 when the housing market had just crashed.
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I spent nine months of nights and weekends working on this disgusting little house with almost no construction experience.
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The worst was on the inside, and I spared you those pictures. I exhausted myself physically, emotionally, mentally, and financially.
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Many nights I lay awake asking myself why I did this to myself. Why did I think this was a good idea? What was the point of all this effort?
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In the end, my reasons weren't sufficient for the difficulty. We finished the renovation and lived in that house for several years, but I burnt out on that project.
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To this day, I have no interest in even the smallest home improvement task.
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Many things in life will be hard, but when you pick an unconventional professional path, it's crucial that you know why you're making that choice.
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If you're like me, you didn't grow up with entrepreneurial parents, so regular full-time employment is probably your default.
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Working for yourself is an unconventional path, so you need to make sure you lay out your reasons ahead of time.
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Here are some examples: I want greater control over when and where I work; I need time to care for children or elders.
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I want time to pursue building a product or service; I need time to pursue educational or personal goals that would conflict with a full-time job.
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These reasons stack together to form a foundation for your motivation. Knowing your why gives you a clear direction to head in.
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It helps you make decisions that move you closer to your goal, giving you boundaries to operate within.
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It's easy to get sidetracked by both the opportunities and the challenges that come up, sending you in unexpected directions.
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It helps you know what you will and won't do; it clarifies your story for yourself and for others.
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We make meaning by telling ourselves and others the story of our lives, both personally and professionally.
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Knowing your why helps you to tell that story. It gives you a way to position yourself in the marketplace.
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It helps you connect with clients, customers, and others. Finally, it protects your motivation.
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It reminds you of what you already decided matters to you and why you chose this path. This helps you build internal resolve to protect against panic and burnout.
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Now let's talk about making the transition. I used to play a lot of Minecraft. If you haven't played before, Minecraft is a 3D sandbox game.
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Sandbox games give you a high level of creative freedom without a single main objective. You can explore the world, build structures, collect supplies, and interact with other players.
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In survival mode, hostile mobs can attack you and kill you. For those of you who have played, think about when players are most vulnerable in the game.
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I would say it's when the sun sets on their first day. The secret beginners don't know is that they have to get busy collecting food, supplies, weapons, and tools.
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They need to build a shelter before that first nightfall, but most beginners just wander around exploring without a strategy.
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Before they know it, night has fallen, and zombies attack them with no way to defend themselves. Experienced players, on the other hand, get to work on those goals as soon as they spawn into a new world.
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They know the importance of gathering resources, knowing the terrain, and building defenses before night comes.
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If you make the jump to indie development, you need a strategy for your transition that will protect you when you're most vulnerable and increase your odds of success.
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Much of this could and should be done before you leave employment. The best way I can illustrate this is with an example.
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Here’s one strategy to help you transition from a regular full-time job to indie development with reduced risk. This strategy assumes you have a relatively stable full-time job that you enjoy or at least tolerate.
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First, if you haven't done this already, focus on making yourself indispensable at your current job. I'd suggest reading Seth Godin's book "Linchpin" and Cal Newport's book "So Good They Can't Ignore You."
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Second, start practicing the skills that so many developers hate: relationship building, also known as networking, marketing, and sales.
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I'm assuming you already have strong software development and project management skills, so you need to work on what’s missing.
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I'll be talking more about this in another part of the framework, but you need to acquire these skills, and the best time to work on them is before your livelihood depends on it.
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Third, land a long-term part-time client that you can sustainably keep, even with your full-time job. This may be a difficult period where you have to work a lot, but it will help you build a financial cushion.
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This last part is the riskiest, but there is always some risk. Approach your employer and tell them you intend to go out on your own, but you would love to find a way to continue working with them in a reduced capacity.
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Present a plan for how you could keep delivering value they care about, but in fewer hours. If this works, transition your relationship from employment to freelance contract, and now you have two long-term clients.
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If this doesn't work, you may need to try again later or look for a second client and make the transition then. This may need to be adapted to your situation or may not work for you at all.
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But the point is you can create a transition plan that reduces your risk exposure and helps you work ahead of that transition to put yourself in the best position for success.
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Whatever you do, don't jump from full-time employment to indie development with cold sales and marketing. You need a network; you need leads coming in, and you need clients and customers.
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You should be seeing a flow of interest before you jump. Also, you want to split your risk across at least a couple of clients.
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You cannot allow all of your work to rely on a single customer. You need to build redundancy in your income streams.
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Now, managing yourself: when I started building web applications, I did some things that are unthinkable to me now. I didn't write automated tests; I didn't use exception tracking.
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I had no performance monitoring or instrumentation. So when things broke, how do you think I found out? Normally from staff or, worse, from customers.
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This is the worst way to find out that something you made is broken. Over time, I learned that I wanted to be the first to know if there was a sign of a problem.
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If we were getting 500 errors in production, I wanted alerts. If there was a slow endpoint, I wanted to know before others complained.
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Ultimately, if there were bugs in my code, I wanted to know about them before they even got deployed. This might all seem obvious to you, but it's easy to forget to apply the same level of scrutiny to our own performance.
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Simply working hard isn't enough; you need to manage yourself. If you've always been an individual contributor, congratulations! You've just become a manager.
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This isn't your full-time job, but it is a role that you must fill. Your clients and customers aren't going to do it for you.
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So what does it mean to manage yourself? At the most basic level, it means doing the work.
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Are you delivering the value that your clients and customers expect? Are you keeping your commitments? Are you earning enough income?
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You're already doing this to a degree in a regular job, but there won't be anyone checking in on you to see how you're doing.
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You need to be checking in regularly with yourself. Thank you.
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Second, improving your performance: while you may be delivering value, you may not be as efficient or effective as you could be.
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At this level, you want to look at how to optimize your daily workflow. Think of ways to improve communication with customers and clients.
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You want to find ways to build more trust and deliver more value, but in less time.
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Finally, this last level is, in my opinion, the biggest potential pitfall, and it was referenced yesterday in a really great way—unattended energy levels and emotional states.
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Ignoring pain—whether physical, emotional, or relational—can lead to serious chronic injury. For example, anxiety around finances, project success, or loneliness due to isolation as a solopreneur.
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Disappointment or depression over a failed endeavor, exhaustion from overwork, or stress. I've personally had to deal with all of these.
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I grew up thinking that attending to your emotional state and making time for self-care was a sign of weakness. But as I've gotten older, I've become convinced it's a sign of health.
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It's essential for an indie developer. Now, I work hard to manage and monitor my emotional health and energy levels to avoid problems.
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You might not like to hear this, but good bosses and managers provide a structure and support system that you're going to miss if you don't build one for yourself.
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You need to manage your time, finances, taxes, client relationships, marketing channels, and business processes while also considering how you're doing emotionally.
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What skills need improvement? What learning investments need to be made? How do you develop and achieve your long-term objectives?
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You will need to manage the increased risks of anxiety and stress stemming from greater uncertainty as well as the risks of isolation and loneliness.
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Your strengths are what you're selling, but your weaknesses are what you build systems and defenses around.
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One of the best defenses I know is to find your own personal team. I recommend having someone in your life who can help you stay emotionally balanced and healthy; this might be a partner or a therapist. I have both.
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I also recommend having someone in your life who can help you work through your business challenges. This might be a mastermind group, a business coach, or perhaps even someone you start a podcast with.
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Finding customers: the most common question I get is how do you find customers? This isn't a perfect analogy, but I've realized that it's a bit like asking how to catch fish.
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The answer is complicated. There are different kinds of fish found in different places. So which kind of fish are you trying to catch?
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Just because you know the place doesn't mean you have the right bait. Different fish need different bait; what kind of bait are you using?
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Just because you have the right bait doesn't mean you're casting properly. You may not be attracting their attention or might be sending the wrong signal completely.
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What's your casting technique? Even when you get a bite, you may lose the fish when you try to reel it in. It takes patience, focus, and judgment.
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Are you reeling carefully? Just because you're doing everything right doesn't guarantee you'll catch something every time. You might go days without a nibble. So, are you being persistent?
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Now, here's where the analogy breaks down: with fishing, you are literally tricking the fish so you can eat it. With clients and customers, your marketing and sales should not be a trick.
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The goal should be a meaningful and satisfying exchange between equals. You need to spend enough time in the right spots, earning attention authentically.
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You’ll build patience and persuasiveness to turn that attention into meaningful engagement. Ultimately, you'll need to make an invitation that leads to a buying decision.
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First, map your skills to market needs. I'll share some examples from a service perspective, but this likely works if you're selling a product.
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Whatever value you have to offer must map to real needs. You could market yourself as a contract web developer, but differentiating yourself from others can be harder.
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It might be better to focus on one or more specific niches. Take stock of your skills and experience to determine your best offerings. Here are some examples: security audits for web applications, fractional CTO for early-stage startups, application performance improvement, and more.
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Each offering may have a different set of potential customers. Next, go where your customers are. Now that you have an offering for a specific customer need, where do those people spend their time?
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Where do they network, learn, or get help? They may spend time on social media platforms like Twitter, LinkedIn, Reddit, or private Slack or Discord communities, email newsletters, blogs, podcasts, and at local meetups or conferences.
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Note that when I say 'customer' here, I mean the person with the felt need for what you have to offer—who can get you to that decision-maker.
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Third, earn attention and build trust. Now that you found where your potential customers are, you need to figure out how to authentically earn their attention.
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Seth Godin calls this 'permission marketing.' He defines it as the privilege of delivering anticipated, personal, and relevant messages to people who want to receive them.
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Treating people with respect is the best way to earn their attention. When someone chooses to pay attention, they are actually paying you with something precious.
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How you earn attention depends on the location and medium. It might involve sharing professional learnings on social media, answering technical questions, writing blog posts, or pitching podcasts.
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You could also create other proactive opportunities and invite people, such as starting your own email newsletter, building a Discord community, or providing free office hours for tech leads.
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You will likely need to experiment as you're starting out. Keep your experiments small with a tight feedback loop, looking for signs of interest from the people you're trying to reach.
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Not everything will work. When something doesn't work, consider why. Struggling with this is common.
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If people aren't responding to what you're putting out into the world, they may simply not see it or not understand it yet.
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They may care, but not know how to respond, or they may know how to respond, but haven't been sufficiently persuaded.
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If you're trying to engage with people across platforms and you're not getting a response, try to figure out where you're getting blocked and practice ways to get past that blocker.
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Finally, make the pitch. You've earned the attention of potential customers, but you still need to invite them to consider how to meet their needs.
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This might involve a sales landing page, but people need to find that somehow. The pitch will differ for each medium.
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For example, in a podcast interview, you might share a service offering with listeners at the end of the episode. On social media, you might pitch when you have availability or announce the launch of a new product.
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If it's connections from a conference, it might lead to a follow-up call to discuss a project. At this point, it's a sales funnel.
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You're converting leads, engaging to determine a fit for your offering and turning some of them into customers, closing the deal, and making the sale.
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Marketing and sales can be really scary, especially if you haven't practiced, and your livelihood depends on it. The good news for indie devs is you don't have to do nearly as much marketing as larger companies.
00:27:41
If you're selling services, you don't have to fill nearly as large a pipeline as a 50-person agency. And if you go after long-term engagements, you may only need to make a couple of sales a year.
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If you're selling products and it's just you, you won't have to make nearly as many sales as a team of full-time employees. Amy Hoy and Alex Hillman underscore this truth in their 30X500 course.
00:28:09
You only need to deliver $30 worth of value to 500 customers to earn $180,000 a year.
00:28:22
Thinking like a business: another one of my favorite movies from childhood is the Disney classic Swiss Family Robinson.
00:28:34
In the story, this family is making a sea voyage to New Guinea when their ship is wrecked on a deserted island.
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After realizing they may not be rescued, they set about creating an elaborate treehouse as their home base.
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They could have just stayed on the beach, watching and waiting for a passing ship, but instead, they set oas up the structures to help settle into their new life.
00:29:09
If you find yourself on the deserted island of self-employment, whether you've been shipwrecked or landed there on purpose, your best chance for long-term survival is not sitting on the shore waiting for rescue.
00:29:24
You need to build a base and create structures that will help you thrive. The first stage is to expand your attention from your core technical work to all parts of your business.
00:29:39
We talked about sales and marketing, but there’s also bookkeeping, accounting, taxes, planning and forecasting, customer onboarding, project management, and customer support.
00:29:52
You don't have to be an expert at all of these things, but you should learn about each one, creating processes and getting help where you need it.
00:30:03
What wasn't obvious to me when transitioning from employment to freelancing was how proactive I would need to be. As an employee, I was good at focusing on my role and doing what was asked.
00:30:16
This just isn't sufficient as an indie developer. You have to think beyond what clients and customers are asking, ensuring that all the tasks necessary for your business get done.
00:30:29
This might involve building relationships, sharing what you're working on and learning, crafting and making pitches, staying in touch, and over-communicating.
00:30:42
You also need to manage your time and costs, forecasting and making projections, celebrating successes, advising, mentoring, doing research and discovery, and running your own experiments.
00:30:57
Now that you've expanded your scope of responsibility, the next stage is to step outside of it all. Go to work on your business, rather than just in it. This concept comes from Michael Gerber's "The E-Myth Revisited."
00:31:12
He explains that people who start small businesses often have a technical background, whether it's baking, carpentry, or interior design.
00:31:26
However, they make a fatal assumption: if they understand the technical work, they assume they understand a business that does that work.
00:31:39
There's nothing wrong with being a technician; what's wrong is being a technician who also owns a business. As a tech owner, your focus is upside down.
00:31:53
The solution is to adopt an entrepreneurial perspective, looking at your business as if it were its own product, competing for customers' attention.
00:32:04
Here's the difference: the technician asks what work needs to be done, while the entrepreneur asks how the business must work.
00:32:17
The technician sees the business as a place people work, creating income, whereas the entrepreneur sees it as a system for generating customer outcomes and profits.
00:32:31
The technician starts with a vision of the present, intending to keep the future much the same, while the entrepreneur starts with a future vision, attempting to change the present.
00:32:45
This isn't easy; I'm still working on this myself. Managing core technical work alongside other responsibilities while stepping outside the business can feel overwhelming.
00:32:56
Sometimes it feels safer and easier just to revert back to simply doing the work of a technician, but this is a necessary step for long-term indie development.
00:33:10
Thinking like a business protects your longevity. It's about building structures and processes that help you prosper for many years.
00:33:23
Now that you’ve learned the secrets of the Fire Swamp, how do you live there happily?
00:33:35
As long as you can avoid the traps of self-employment and make a decent living doing good work, there's no reason you have to do anything else.
00:33:46
But if you're ambitious or tend to get bored easily, you'll probably need a plan to level up.
00:34:01
First, watch your indicators or gauges. These include money, cash flow, and reserves; capacity with your skill set, knowledge, and expertise; interest, which relates to enjoyment and curiosity; and impact, referring to your broader long-term effects on your community.
00:34:14
These indicators often rise and fall independently. For example, your income might be high, but your interest might be down.
00:34:27
You can't force these indicators to change directly, but you can treat them as signals of what your solo business needs, making adjustments to your systems accordingly.
00:34:39
While making those adjustments to maximize your indicators, you may still feel unsure of your direction.
00:34:50
In a company, there might be a clear career ladder for you climb or a manager helping you progress. As an indie developer, there is no preset path to follow.
00:35:05
You may not have a path, but you can find models. Seek out other indie developers doing work you admire and learn how they've done it.
00:35:18
Look for models that are one to two years out as well as those five to ten years out.
00:35:27
These are just a few examples from the Ruby world. Transitioning from just starting out to being a seasoned indie developer can be filled with difficulties.
00:35:42
We've learned the secrets of the Fire Swamp, along with protective measures to keep our solo businesses afloat: knowing your why, making the transition, managing yourself, finding customers, and thinking like a business.
00:36:00
And we've had a brief look at how to go beyond merely making it to thriving. Now, I want to leave you with some takeaways.
00:36:14
If you're already an indie developer, did you identify any areas where you could better protect your downside right now? What could you do about that?
00:36:25
If you're predicting all your downsides, which gauge or indicator is currently the lowest for you: money, capacity, interest, or impact? What could elevate that?
00:36:36
If you're considering the indie path, have you built your primary skill set to reliably deliver quality work with little supervision?
00:36:50
If that's progressing nicely, how might you start connecting and being helpful to others without leaving your job? How can you practice marketing and sales skills?
00:37:03
Is it time to draft a rough transition plan?
00:37:14
If you're happily employed, are there any circumstances that might cause you to explore the indie path? What if you made a small investment based on that likelihood over the next year?
00:37:28
After all this, you might still wonder why you should care, especially if you identify with that happily employed group.
00:37:42
Let me tell you why I care and why you should too. First, I care about developers who need options.
00:37:55
Childcare responsibilities can make full-time employment difficult. Job location conditions might impede the dream of traveling the world.
00:38:07
Maybe there’s no position that aligns with someone's unique skills and interests, and they need to create their own.
00:38:22
Second, though I don't know the future, the world may be moving away from long-term full-time employment as a work default.
00:38:36
Remote asynchronous roles are becoming more common, and waves of industry layoffs show that a regular job isn't necessarily a safe one.
00:38:49
This likely suggests both more opportunity and increased demand for contractors, consultants, and fractional workers, alongside those building products.
00:39:02
Finally, I believe our industry, and the Ruby community specifically, will be better served by diversification.
00:39:17
Our community is a diverse ecosystem with potential niches ranging from large companies to independent developers.
00:39:31
A healthy ecosystem encompasses all its niches and thrives with a populace of happy, productive, and profitable indie developers.
00:39:46
If this resonates with you and you wish to talk more, please reach out! I'm not an expert on all of this, but I'm passionate and enjoy discussing challenges and sharing my experiences.
00:40:01
I'd love to help or encourage you if I can. Finally, here are some books and resources that have informed this talk and my broader perspective.
00:40:13
Here's how you can get in touch with me too.
00:40:24
Thank you.