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The Imposter's Breakthrough

Are you a self-taught developer that feels you don't belong in this industry? That feeling is holding you back and damaging your career. Come work with me, one on one, and we'll fix that.

Thanks for dropping by and learning more about this new venture of mine. I don't want to spend a lot of words in a preamble, so I'll get right to it:

I want to help you break through your personal barriers and transform into the professional you want to be. Give me 6 weeks and you'll be free.

If you're here, reading this, it's likely you're self-taught like me and have a deep-seated feeling that you don't belong in this industry. Or, at the very least, that you've been fooling people pretty well up until now and risk exposure if you keep going on. Either way: this feeling is holding you back.

I've felt all of these things. I have found myself shutting down during meetings and social events for fear of being outed by my own mouth. I sat in the back of the room during meetings, and nodded along as colleagues of mine discussed things far, far over my head.

Me, sitting between Jon Skeet and K. Scott Allen, pretending I know what they're talking about.
Me, sitting between Jon Skeet and K. Scott Allen, pretending I know what they're talking about.

I taught myself everything I needed to know in order to get a job done for a client, for my company, or for my boss. I focused on delivery and told myself that shipping was the important thing - understanding sorting algorithms was academic and stupid. I felt good about this decision, but then I also would run and hide when conversations turned theoretical. I felt shame.

I don't like shame. So, in 2014, I decided to turn my learning skills inward and teach myself the topics I didn't know.

I learned a lot, grew a lot, and became a completely different person. I want to share this with other people, possibly you, to help you have the same "awakening" to this amazing career and all the possibilities that are here for you.

The Offer

To the point: I'm offering a 6-week interactive program where you and I will work closely together, with the goal of getting you past your internal road blocks.

Specifically, we will:

  • Get personal. I'm not a therapist, but I have spent an absolute ton of time digging into my internal thought process and emotional barriers. I'll get into this more below.
  • Reverse the downward spiral of Imposter Syndrome by arresting the process, taking stock of where you are in life, and then unwinding the psychological burden you've put on yourself by actively taking you out of your own mind.
  • Build the CS foundation you lack, backfilling concepts, software practices, programming principles, history, and theory - all with a focus on how this applies to your day job. You will be studying constantly, and I'll be right there with you, supporting your efforts.
  • Share what you've learned, through journaling, blogging, or even speaking to local groups. Maybe it's just a lunch-and-learn at your office, but giving back is critical to the process. If you're uncomfortable working with people, maybe you explain things to your partner or pet!
  • Chart your path forward, whether it's moving up in your company, becoming an authority in your field, or starting the side-hustle you've always dreamed of, we'll figure out a path for you moving forward, and how you'll get there.

By the time you're done, you will see yourself, and your career, completely differently.

Hokule'a, the surfing cat. If he can, you can.

You might be thinking: Rob, this sounds interesting, but it's also not terribly specific. What, exactly, are we going to do? That's a great question (well done). 

Here's the deal: I'm forming this program together with you. This is the "Founder's Cohort", which basically means that I have a plan, but it's flexible and we'll be building things together. We'll see what works for you, what doesn't, and build what makes sense. I've lowered the price because of this, added more personal hours, and also reduced the number of folks I'll take on for this first effort.

I'll explain more in a minute - for now let me go into a little more detail on what you can expect.

What This Program Is

You'll be working with me, directly, on a weekly basis for 6 weeks straight. You'll have unlimited chat access (Signal, WhatsApp, Slack, email - whatever works) with a promise to get back to you within an hour provided it's during work hours (9-5 HST).

Define: Imposter

We'll meet for at least three hours every week; 1 or 2 sessions with me, and one with the larger group (which, for now, will be capped at 5 people). The personal sessions will go over your progress, and focus on upcoming tasks. The group session will be accountability sessions, where we support each other and share our wins and struggles.

The main thing we'll do is eradicate your Imposter Syndrome. If you're not feeling like an imposter, then this program isn't for you, but I do appreciate you dropping by! I have helped countless people do exactly this indirectly through books and videos I've made, and I can shorten the process for you if we actually work directly, helping you achieve the goals you have for yourself in a much faster time (with a lot more fun).

At the end of the 6 weeks you will either be completely changed, or you'll have your money back. I shoot straight and am not in this for the money, but I'll be honest, if I never work another day at a big tech company or a clownshow startup, well, that would be wonderful.

What This Program Is Not

I'm not a guru and I'm not here to blow sunshine. This isn't going to be a routine Zoom call where I tell you a secret formula and you all of a sudden "see the light".

I don't have any answers for you and I can't promise you'll know whether P = NP when you're done. You'll get back exactly what you put into it in terms of desire and motivation.

This program is about you, and the only person who can make it a success is you, which is why I'm being exceedingly selective and only allowing 5 seats in this "Founder's Cohort", which I'll discuss in detail in a second.

If you're still interested, read on...

Personal Growth

The core of this is going to be psychological, there's just no way around it. I'm not a therapist and we're not going to spend time talking about your childhood, but I am a great listener and will reflect back to you what I hear in terms of your professional life, and ways that you can move beyond the toxic crap holding you back.

You will go on a journey inward, and I'll give you weekly tasks that are specific to you and your situation. These tasks could be anything from a set of journal prompts to randomly engaging in meaningless conversation with a stranger. Perhaps making dinner for yourself or getting to know a maintainer of a large open source project and helping them with their issue list. These tasks will be based on your weaknesses, and geared towards you confronting them, moving through them, and freeing yourself.

The main thing, however, which you should know up front, is this: we're going to destroy your Imposter Syndrome starting on day one. The first step will be for you to see clearly, and admit out loud, that you are toxic. Toxic to yourself and toxic to everyone around you when you start letting your doubts and fears tell you that you don't belong. When you give in to this nonsense you pull group energy into you, all in an effort to fill the holes in your emotional state of mind. 

This is going to be a tough process, and if you're not willing to do the work, this program isn't for you. Imposter Syndrome is not humbleness. It's not "being aware of your limitations" and it most definitely is not healthy. It's a defense mechanism that erodes a positive group dynamic, gives you a false sense of humility, and compounds upon itself until you drive everyone around you crazy. It needs to be destroyed with fire!

So, how do we fix it? We start by seeing the behavior clearly, and then rebuilding our thought patterns through focused effort and repetition. This takes time, and I'm here to help you through it all, showing you the exact process I put myself through. That process is simple: do what scares you.

Don't quit, don't give up

Once that's done, we can move on to the good stuff!

Professional Growth

The goal of this program is to help you transform so you can make a change in your professional life. It's great to master your insecurities, but you're also going to need to focus outward as your inner resilience kicks in and you once again become the self-assured super star that you've always been.

We'll start by backfilling any core skills or knowledge you don't have. No CS degree? No problem! I have resources for this that you will study, and when we come together I'll drill you on them and also answer any questions you might have. We'll go over conversational tips and pointers on technical topics you might regularly face  (Big-O if you're interviewing, CAP theorem if you're a data person, etc.). The goal isn't to make you a CS professor, it's to give you enough detail that you connect the dots and can hold your own when things get theoretical.

CompSci Baby

I'm not here to give you lectures or spend hours walking you through Merge Sort, I am here to help you build your confidence so you can have these discussions and feel like you not only belong, but are a vital member of the group!

Expanding Your Reach

With confidence gained and your CS skills on fire, you'll be ready to chart your path to the next phase of your career.

If your goal is to move up at your company, venturing into leadership or taking on more senior roles, we'll focus our efforts on building your social skills. It's not enough to be good at your job, you need to mold consensus and learn to "play the game" that all senior folks do. 

I'll show you how to lead a team and inspire others, leading from both the front and also the back. Leadership can be incredibly rewarding, but only if you know you're the right person to lead, which you probably are, because you're here reading this. You want this for your career, which is a great place to get started. 

If your goal is to break into the world of content creators, speakers, or authors, I can get you started on the right foot as well. This program isn't about setting you up with the ultimate home studio and molding your vocal skills - it's about getting you into the right frame of mind so you can build those things for yourself.

A speaker giving a technical presentation to a large crowd at NDC Oslo
You, someday, if you wish

It takes a lot of courage to step into the public realm, and that's what we're going to focus on. You don't need to know everything before you start, you just need to know you don't know everything and have a willingness to learn openly, be humble, and embrace vulnerability.

The thing people respond to most is authenticity. We like authentic people because we feel we can trust them, and if we trust them, we connect with them. This goes for a professional life in public, and a leadership position at your company. Authenticity happens when people feel good in their own skin and believe that their opinion matters.

When they free themselves from toxic defense mechanisms like Imposter Syndrome, and that's just what I'm here to help you do.

Speaking of...

Who Am I and Why Do I Think I Can Help You?

If you're reading this note, you probably know who I am and what I've done in my career, which is exactly the point. I want to help you get there, so people know the same about you.

On a more personal level, you might be wondering why I think I can offer you help with Imposter Syndrome, insecurities, and emotional intelligence. I'll share that with you now.

I battled with Imposter Syndrome for far, far too long. It still pops up, from time to time, but I recognize it for exactly what it is: something to let pass through me. I was disabled by it for most of my career, until I realized just how toxic this feeling really was.

Me, with the late K. Scott Allen at a conference in Norway, making it up as I go
Me, with the late K. Scott Allen at a conference in Norway, making it up as I go

Let me explain more.

10 years ago I sold my business, Tekpub, and decided to do a "mini-retirement". This is when my life started to fall apart. My then-wife demanded we move away from Hawaii, where we raised our kids, to Seattle, so she could get a Masters degree and become a Dietician.

I didn't want to move to Seattle. I fell headlong into depression which was compounded by the darkness and rain, and also the loss of the work I cared deeply about: creating online video content for programmers.

In 2020, at the onset of the pandemic, my wife and I separated after 30 years of friendship and 21 years of marriage. We divorced shortly after, and my kids went off to college. I had to deal with the double-life-trauma-whammy of going from a full family to being completely alone in an empty nest within the span of 3 months.

That's when I started reading books about psychology, philosophy, emotional resilience, behavioral adaptation, how to get rich, and more. I became obsessed with understanding my thought processes and why I made the life decisions I did that put me in that strange situation. I lived in a beautiful place that I fought to be in (Kauai), with a beautiful family and work that I was proud of. That had somehow changed to living in a dark, 1-room apartment in a suburb of San Francisco, all by myself, with a soul-sucking corporate job.

We are the product of our decisions, and in some way, shape or form, a chain of decisions led me to that place. I needed to understand how and why. So I bought every single book I could on the human experience, from philosophy to religion to emotional health and more.

I dug into Eastern Philosophy, reading books by Thich Nhat Hnan, and Pema Chodron, and went right out of my comfort zone reading Radical Acceptance by Tara Brock and Man's Search for Meaning by Viktor Frankl.

I also explored what it meant to "be a man" as I was on my own again after so, so long, reading Iron John, The Way of the Superior Man, Can't Hurt Me, Never Finished, and No More Mr. Nice Guy. I read about self destruction and toxicity, including an amazing book on self sabotage called The Mountain Is You by Brianna Wiest and The Confident Mind by Dr. Nate Zinser.

Here's the full list of personal development books that I've read over the last few years:

My Audible.com library of personal development
My Audible.com library of personal development

As my understanding deepened, I branched out into my financial well-being and building my career. My savings were destroyed from my divorce and I had exactly 3 months of runway to live on if I lost my job. I was worth well over 7 figures just a few years prior, and now I had next to nothing. Again: how did this happen?

That's when dove into books that focused on all kinds of growth topics, including investing, career theory, and digital marketing. Books like The Psychology of Money, How to Beat the Stock Market, Rich Dad, Poor Dad, Set For Life, The Millionaire Fastlane, I Will Teach You To Be Rich, and more. In terms of marketing, I devoured books by Russel Brunson, Shane Melaugh, Seth Godin,  Jeff Walker, Graham Cochrane, Joel Erway, and many more whose names I can't recall.

Again, here's my Audible.com library:

My Audible.com library - financial and career books
My Audible.com library - financial books

I've Been There, I Can Help You

My point in telling you this is straightforward: I am on a massive quest to rebuild myself psychologically, and it feels good. I learned a lot. In fact I joked with my therapist that I probably knew enough to switch seats with her, to which she answered "no shit Rob. Your desire to learn is pretty incredible".

I put the same dedication into learning about self-knowledge and self-care that I did learning CS concepts with The Imposter's Handbook. In fact, I would say I went at it even harder.

I truly believe that I can help you, by sharing what I've learned over the last 20+ years of my professional career, as well as the last 7+ years of my personal life. These aren't simply words: this program is my challenge to myself as well, to get over the idea that I don't know enough to be able to help others like you.

The Application

As I said above: I'm being very selective here, I need to know that I can help you. This is my first go at this, which means you'll need to be patient too, which is why I'm cutting the price in half for this initial "Founder's Cohort".

We start with you copying/pasting the text below and letting me know a little bit about yourself. If I feel I can help you, we'll set up a time to chat face to face. If it works for both of us, we start.


Tell me a little about yourself.

(Your background, how long you’ve been coding, what your current role looks like.)

What do you struggle with most right now in your career?

(Imposter syndrome, confidence, technical gaps, company politics, etc.)

If we were sitting down 6 weeks from now and you felt totally different about your career, what would that look like for you?

(What would change? How would you feel?)

Why does this matter to you now?

(Why not wait another year, or try another course? Why now?)

This initial program is a $6,000 investment. Are you in a position where that feels doable?

(This isn’t about squeezing you — it’s about making sure it’s realistic for you.)

Anything else you’d like me to know?


I can ride dragons!

Questions?

I'm happy to answer any questions you have, but know that right now this program is already reduced by 50% and I'm not in a financial position to go further. In the future I hope to open up pricing parity and other options for people who need help. For right now, I need to focus on getting this thing off the ground.

Thanks for reading!

PS: Yes, I wrote every word of this text. I would never trust any LLM to write something that comes from my heart. And this most definitely does.