People Tech

Frequently asked tech career questions

I’ve reached the point in my career and have enough gray hair that people sometimes ask me for career advice. Usually they are in tech, trying to make a transition into a different role, or are trying to get into tech. I do my best to answer these questions because it is obvious that they have experienced some sort of trauma and/or have run out of better options if they are at the point where they can look into the melancholy and barely obscured madness behind my eyes and think “This is someone who can help me.”

To save others from having to brave the same journey, here is a small FAQ that reflects the common themes of those discussions.

How do I get started in X?

You just do the thing and keep doing it until someone is willing to pay you money to do it.

You become a writer by writing.

You become an engineer by engineering.

Unless you need a license (*I* won’t judge how you learned to remove appendixes, but others might.), you just need to start doing the thing.

This is not the answer people want or are looking for. But it really is that simple. There are no shortcuts or lifehacks. Simple != easy and that sometimes makes our brains sad. I’m sorry.

What tech do I need to learn to do X?

There are admittedly different fundamentals required for different types of jobs, but if you’re asking about specific technologies the answer is that it doesn’t really matter.

Python or Ruby? Doesn’t matter.

AWS or Azure? If you can figure out one, you can figure out the other.

If you have a specific role in mind, do some research on the thematic pillars of that role and pick 1-2 pieces of tech in each pillar to focus on. Do not go down the rabbit hole of infinite research trying to decide on the perfect lineup of tech to learn. That’s not a thing. You’ll just delay doing anything useful.

There is one “trick” I recommend here. People have mixed opinions about certifications, but if you can use studying for a target certification as a learning path, go for it. It may focus you a bit.

When is it OK to list X on my resume?

Have you made a thing or two that worked using X and can speak about it in the appropriate context? OK then, go for it unless the job was explicitly defined by X, like “Unity Developer” or “AutoCAD Tech”. The ancillary stuff is fine to list if it is relevant to the role and you have actually used it.

Is X just a word you saw somewhere? Do not put it on your resume. I generally don’t delight in making people squirm in interviews, but I will create a “learning moment” that may be uncomfortable if I catch someone keyword stuffing.

How do I answer interview questions about things I haven’t done without lying?

I have never lied in a job interview. I have, however, re-framed my experience in the context of the job I was applying for.

When it comes to the actual interview where you’re asked “Have you done X using Y?” and the answer is “No”, try going with “I’ve done A using B which is very similar to Y” – shifting the focus to how you solved a similar problem rather than the specific one they asked about. Granted, you can’t pull this trick for every question without coming off as evasive, but it’s a legit tool.

It’s also OK to not volunteer unprompted caveats like “I’ve done X… but never in production.” They don’t need to know that. You aren’t marrying this person. Just say “Yes” and move on.

Nailing an interview is more about being able to sell yourself than proving what you know, with exception of coding interviews which are a crap shoot (I prefer take home exercises.). The “selling” part feels icky to a lot of us, but it shouldn’t. All you are saying is “I’m worth hiring and would or could be good at this.” not “I am the platonic ideal of a human.” Selling your value isn’t lying, it’s being honest about your worth, which may require you working on liking yourself.

If you don’t have *any* experience and have made it to the interview stage, the person interviewing you either knows that or is an idiot. You should be good in either case, although I would recommend not working for idiots. It is in your best interest to be honest (generally, but especially in this case) about your lack of experience (again, don’t volunteer answers to unasked questions) because it will be very easy to sniff out a lie – assuming you’re not with the idiot.

I feel like I’m under qualified for all the jobs I look at.

To be fair, this is a statement and not a question, but here’s the rub:

Don’t assume that everyone applying for or working in a job knows more or is more experienced than you.

“Think of how stupid the average person is, and realize half of them are stupider than that.” – George Carlin

Some of those stupid people have the job you want. They may have even got the job because of how oblivious they were to their own weaknesses and came off confident as fuck.

Regarding “job requirements”: ignore them past how they frame the nature of the role. In most cases they are an aspirational wish list that someone copy/pasted from someone else’s aspirational wish list. That folks often ask for more years of experience in a specific tech than the tech has existed is testament to the lack of thought that goes into most postings.

If you see a job description and immediately think “I’m qualified for this.” you are probably over-qualified or very senior and have an appropriate level of confidence.

When I write job descriptions I try to use the requirements to filter for “I need you to be somewhat familiar with this branch of tech.” vs. “I need someone with exactly 5 years of experience writing Terraform.”

On paper, I’ve never fully met the requirements for the roles I’ve been hired for. I don’t even have a college degree and sound like Hank the Cowdog when I talk. Don’t let the “requirements” stop you from applying for something.

I mean, they let me in. You’re probably way nicer than I am.

It says “senior”. I’m not a senior.

Again, not a question.

Here’s a secret. Job titles are bullshit. Ignore them.

Their functional purpose is almost entirely for creating pay bands. Just work hard, be kind, remove bottlenecks, and solve pain points.

Ignoring your title and the scope that it implies can carry your career a lot farther than trying to adhere to some rigid definition. Stretch your wings and get involved in whatever interesting work you come across. If you approach work that wouldn’t typically fit your title with humility and thoughtfulness, you will generally be welcome.

Summary: The stakes are low

If you’re reading this, it’s unlikely that you’re in a situation where getting a specific job is literally the difference between life or death. To paraphrase the mostly problematic founder of GoDaddy – No one is going to eat you if you fail.

Apply for roles that interest you. Pitch yourself with confidence. Learn something from every interview, whether you get the job or not.

And when you do get the job, reach a hand back down the ladder to help someone else up.

Photo by Andre Mouton on Unsplash

People Tech

You are not your code

You… are not your code. You are not your configs, your documentation, your blog posts, your conference talks, or your job.

You. Are. Not. Your. Work.

I say this as someone who spent many years of my life deriving personal value from the work I produced. It started in angst-y teenage writing – “No one understands me. These words are my true self.” – one of the dumbest of youthful ideas, possibly only surpassed by “I need to hurt to create.”

I took it into my career. “I am only good if I do a good job.” And I spent years feeling like crap about myself because my work was never as good as I felt it should be. I took other’s criticism “well”, but only because I absorbed it and later amplified it through my own lens. If something was wrong with my work, it was a personal flaw and I needed to fix it. Note taken.

This is bullshit. The sooner you internalize this and integrate it into your everyday, the better. Your job is a role you play, a hat you put on, a thing you do. The things you produce – code, writing, whatever, are at best a watered down reflection of your thoughts at the time – an artifact. (Worth noting: you are also not your thoughts. They are just things you temporarily have, but that’s a much bigger can of worms.)

Your value as a person is independent of all these things. You can produce garbage work and be an amazing person. You can produce amazing work and be a less than amazing person.

We grow up hearing “actions speak louder than words” and wrap that idea around our work reflecting who we are. I don’t think that’s the intent of the message, which has more to do with relationships and personal interaction than work.

As we develop in our craft and inherently pour more of what we view as our “selves” into our work, it becomes harder to keep those ideas separate. We learn to handle criticism from peers and managers, through code review, general feedback, or editing, by developing “thicker skin”, which in most cases just means walling ourselves off. This is the wrong metaphor and ineffective anyway. Thick skin won’t protect you from yourself. Very few of us are taught how to handle that criticism.

Turns out, rather than thick skin, you might be better off with a spam filter, something that can differentiate between commentary on your work and commentary on you. Something that can detect the intent, spirit, and context of feedback, internal or otherwise, and classify it accordingly. “These messages get delivered to the inbox to be considered for future analysis. These other, not-useful messages get delivered to the tire fire next to the empty field where my fucks grow.”

We (tech people) are generally terrible at these distinctions. Part of it is due to the visibility of our work among peers, part of it is rampant workaholism, part of it is the isolation inherent to “deep work”, part of it is that many of us belong to a generation of emotionally damaged latch-key kids. There are a multitude of reasons and they manifest themselves in a strange form of conflict aversion where we have massive reactions to criticisms of our work and don’t push back at all to actual personal attacks.

I haven’t mastered this. I struggle every day but I keep trying because I’ve felt the truth of it and the alternative is unsustainable (Like, literally, I would die.). When you’re able to have a clearer distinction between yourself and your work, and in turn, commentary on yourself or your work, things stop feeling so bad.

You don’t need a daemon to make you feel like a bad person for writing bad (whatever that actually means) code or not performing up to some standard (yours or others’) at work. Shut that shit down.

Be proud of your wins. Learn from the misses and then set them aside. If doing “good” work is actually important to you, you’ll be much better enabled if you can redirect all that emotional energy you’ve been spending criticizing yourself or dealing with others’ criticism by funneling it into being kind to yourself and seeking value elsewhere.

Photo by Daniil Kuželev on Unsplash

Learning People Tech

What I love about SRE

My childhood was soaked in science. As I learned the alphabet and how to tie my shoes, my dad spent his days taking water samples and caring for the fish that made up the research cohort for the aquaculture study he ran. We lived at a research site on the lake and I toddled along through three hot summers, staring into the eyes of whiskered catfish and witnessing the hard, mundane work of science interwoven through our daily lives.

I did a search recently and the only monument to that time I can find is an eight page document that basically says “meh”.

One morning, years later, I sat in my dad’s lab injecting nematodes into hundreds of tiny, clear Dixie cups full of dirt samples, some of which would later be paired with marigold extracts. It wasn’t the most exciting “Take your son to work” Day, but once I developed a cadence there was a calming quality to it and time melted away.

It was more interesting to me as an adult, when I learned this type of research, as boring and un-sexy as it is, impacts whether millions of people get enough to eat.

Our living room and porch were filled with hybridization experiment rejects – peppers, squash, and random erosion-control plants in an assortment that would in no way be considered normal by anyone who actually raised house plants. They were misfits that didn’t have the right taste, shape, structure, or hardiness to make it to the next round and the smell of their potting soil and green of their leaves transformed our house into a primordial jungle. For all of my dad’s commitment to the logic of science, a bit of animism also threaded through his work. He’d feel bad if he had tilled these plants back into the dirt or tossed them into an incinerator.

These “failures” were each data points and lessons. Some of those lessons were “don’t touch this and then rub your eyes”.

All of these objects and experiences embedded a system of discovery in me (Some might call it a method 😜.): make a guess -> try to prove your guess wrong and measure the results -> analyze and iterate. This method is a tool that helps reveal the fabric of reality. It’s the best thing humans have ever come up with.

Growing up surrounded by the practices of science taught me to find interest and beauty in the outwardly mundane, that there was opportunity, even in the most boring-seeming places, to discover something that no one else in the whole world knows – at least for a brief moment.

This kind of childhood inspired me to be curious and persistent. Other aspects of growing up weren’t great but this part of growing up was as close to perfect as I can imagine and I am grateful for it.

My career has meandered its way not into the biological or physical sciences, but into something we’re currently calling site reliability engineering – a strange amalgam of systems administration, performance management, software development, quality control, and the crafting of antifragility, a practice I don’t really know what to call other than “applied statistics”. In the narrowest view, SRE can be limited to a fancier name for release management, but in most organizations there is runway to make it much more.

As with any maturing discipline, people find different areas of focus, but the aspects of SRE that appeal most to me are those that mirror what I saw growing up, areas where the scientific method can be leveraged to chip away at problems that have, up until very recent history, only been attacked with intuition and business process consultations.

SRE doesn’t hold a monopoly on this approach. Anyone can start challenging assumptions with “What do we think is true and how would we know we’re wrong?” questions, but there are some unique, SRE-specific opportunities for experimentation at scale and within the distributed systems that SREs manage. And because of its inherent technical nature and practitioners’ comfort with data, SRE (along with data engineering and finance) provides a good beach head for science to wiggle its way into the rest of a business.

Science manifests itself in SRE in expressions as simple as “How do we measure and increase reliability? When and where do we encounter diminishing returns?” That’s a good place to start, but not where anyone should stop. Continuing the line of questioning of “What matters to us and how do we keep ourselves honest?” provides a lot of opportunities to provide value and make interesting discoveries.

Questions you ask could lead you to dig into cloud provider bills, or analyze access patterns to blob storage, or purposefully inject failure into systems to find their weaknesses. Managing servers is part of the job in a similar way to my dad having to feed the fish he was studying. It’s a base requirement, but it’s not the point.

The really interesting opportunities in SRE present themselves when you open yourself up to a broader definition for your role, what questions you should be asking and to whom. Thinking more broadly than what you need to do to address the bottom tiers of Maslow’s hierarchy of needs for systems operations allows you to affect change and make useful discoveries. This is where I thrive and find the things I love about doing SRE work – having real things to measure, make decisions about, and improve through a methodology that requires you to be honest about the world you live and work within.

People Tech

Dirty secrets of DevOps

I’ve read dozens of DevOps success stories, tales of bold IT leaders transforming their business and steering big corporate ships into the future. It’s hard to avoid all these stories about “DevOps transformation” and how some guy named Jim pulled the IT department out of the stone age. The trades, blogs, and conference presentations are filled with them.

No one talks about the failures though, very few even write about their struggles implementing DevOps. It’s all sunshine and rainbows, which sucks, because that isn’t real.

Success teaches us little other than survivorship bias and how to feel bad about what we haven’t achieved. Failure and hardship are where we learn. That’s where the good, meaty stuff is.

So here are a few dirty secrets of DevOps.

Most companies that say they are “doing DevOps”, aren’t.

Because of all the success stories (real or imagined) that have wiggled their way into the minds of CXOs, “we should be doing DevOps” became an empty corporate directive that inspired thousands of executives to start calling their IT infrastructure groups “DevOps” instead of “Infrastructure” or “Systems” or “Operations”.

Unfortunately, this seems to often play out as “We’ve renamed the group, so we’re going to be letting most of the team go, because we’re DevOpsing all the things now and being lean and mean. Also, the developers are still a separate group and they’ll be throwing more stuff over the wall to you.”

So you end up with a few overworked, traditional Ops folks trying to keep the wheels on the bus with zero changes to the way work is managed or how the IT group functions day-to-day. Their manager is shouting down the hall about automation while the poor Ops teamis trying to pivot a SAN-installing, server-racking skill set into something that looks like a cave-man version of coding.

The only metric that improves in this scenario is “personnel cost”, and only temporarily because burnout and churn spike, driving up staffing costs a few quarters down the road. But it looks good long enough for someone to say “See, we did it!” and feel validated.

Even if you get the “IT folks” on board, getting plugged into the business so DevOps practices can benefit other groups and the overall bottom line comes with its own challenges.

Fixing this issue requires a lot of skill managing upward and sideways. Often times, it’s not worth trying to change and moving on is a better option. Your mileage may vary.

Implementing DevOps is Really Fucking Hard™

DevOps is all about people and process, getting everyone working together to do fewer dumb things, and smart things faster.

Historically, getting people to work together and not be jerks to one-another has been a bit of a challenge. Humans achieve awesome things when we collaborate (like spaceships and lasers), but we usually suck at working together. Because of that, I’m always impressed when I come across an excellent people-whisperer, someone who can motivate different groups to work towards a common goal without burning down each other’s village.

Problem is, there’s like five of those people on the face of the planet and chances are, they don’t work for your company. You might have lucked out and have 1 or 2 folks who are kind of OK at people-wrangling and peace-keeping, but most businesses (especially the bigger ones) seem about three seconds and a passive-aggressive sticky note in the office kitchen away from an all out blood bath.

Assuming you can get people working together, you’re now faced with the challenge of implementing process. You probably have one person on your team who loves process. Everyone else hates process and that person.

You’re never finished

There’s no such thing as “we achieved DevOps”. It’s a practice like healthy living or Buddhism. There has to be a champion(s) on your team who pushes every day to make things better.

When someone talks about DevOps success, what they’re really talking about is achieving flow, that there is a functional work process in place that is continually measured and improved upon. It’s an ouroboros value pipeline.

That’s not something you can arrive at and stop tending to. Without constant care and feeding, the processes you worked so hard to implement will start to die off.

No champion, no DevOps.

All that being said…

None of this means that DevOps isn’t worth doing, just that you need to be realistic about the challenges you’re going to face. I’ve leaned on hyperbole pretty hard to swing the pendulum away from sunshine and rainbows, because reality is somewhere in the middle.

Getting Dev and Ops (and Security), groups who have traditionally walked down the hall waving their middle fingers at each other, to 1.) work together and 2.) implement and adhere to process, will likely be one of the most difficult things you’ve attempted in your career. You have to put a lot of work into making the right things the easy things, reducing friction wherever you can. Setting mandates or badgering doesn’t work, you have to sell the value.

Getting top-down buy-in (and understanding!) of true DevOps/Agile practices is hard. It requires reorganizing groups and a sustained sales pitch to all involved. The need for this trails off a little once the business and IT staff start seeing value, but expect it to be a long, sustained effort. I’m always a bit dubious when I hear something like “we transformed IT in three months” – either that group really has their shit together, someone is lying, or we’re not using the same dictionary.

For practitioners and evangelists, these are the things we need to start talking about more. There’s a slick consultant vibe that’s weaved throughout discussions about DevOps that glosses over the practical and prescriptive. Too many of these conversations focus on high-level what-to-dos and not enough on concrete how-tos and context, especially when it comes to people-centric issues.

People Tech

How to lead without authority

I spent a lot of time being angry when I started my career. My employers and bosses frustrated me. My coworkers frustrated me. End users, customers, everyone frustrated me.

I got angry about decisions that made no sense to me. Most of my complaints fell into the theme of:

“If I was in charge, we’d never do X.”

If only they’d asked me first. If only I was the boss. If only…

I probably had a few legitimate criticisms and good ideas, but most of my frustration was based on the ignorance of youth and inexperience — thinking I knew more than I knew.

When I did want something changed or disagreed with a decision, my first course of action was to complain to my boss.

“This is stupid. You should fix it.”

I had no sense of agency and thought I couldn’t change anything because I didn’t have the power to. I could come up with ideas (Fun fact: ideas are easy.), but I needed someone else’s permission and authority to put them into motion.

I thought I needed control and a mandate to lead and affect change. More often than not I thought “I can’t do anything about this, other than complain.”

I was wrong.

Over time I discovered three things:

  1. True leadership is not based on authority.
  2. It’s possible (even preferable in many situations) to lead sideways.
  3. The degree to which anyone has actual control over anything or anyone is comically small.

Getting people to follow you

I’ve been very lucky in my career to have worked for good managers, although I often took them for granted. Even though I looked to their authority for solutions, with only a couple exceptions did any of them ever tell me “Do this… because I said so.”

Rather than dictating specific action, they presented a vision of what needed to be accomplished (goals), and provided me with support and breathing room to get it done. They trusted and empowered me. They made me feel important and that they genuinely cared about my well-being and personal progress.

I still thought I needed their mandate to change things, but I was able to move out of my comfort zone and build confidence in my skills and judgement.

My motivation to do well flowed from a desire to not let those managers down. I didn’t want to betray their trust or make them look bad. None of that dedication came from fear of losing my job or a respect for authority — it was because they inspired me to care. If any of them called me today and asked for help, personally or professionally, I’d be there in a heartbeat.

On the flip side, I’ve had a couple of bosses that micromanaged me (making me feel like they didn’t trust me at all) or leaned heavily on their authority to drive me and coworkers to action. I respected neither of them, although I have some sympathy for them in hindsight.

I’ve come to believe that there is no surer sign of a person’s self-perceived inadequacy — feeling in-over-their-head or simply out of control than when they feel the need to declare themselves “the boss”. The moment a person asserts their authority as the reason to follow them is the same moment they’ve proven they aren’t worth following.

I’ve seen that behavior in pimply-faced kids who get promotions at fast food restaurants. I’ve seen it in 60-year-old CEOs of large companies. Everytime I see it, I want to pull those people aside and tell them “Shhh… Shhh… You’re OK. It will all be OK.”

Then I’d tell them three things about what real leaders do:

  1. They provide a vision of something greater than day-to-day tasks.
  2. They spend the time and emotional effort to discover what the people they’re leading care about.
  3. They trust and empower the people they’re leading, even when the stakes are high.

The scope of what can be accomplished by people who are inspired and care about the person leading them is far greater than what is done out of fear of losing one’s job or being reprimanded.

The power of soft influence

Even working for good bosses, I remained under the impression for a long time that my power to drive change had to come from them.

Yet again, I was wrong.

Without really being conscious of it, I started copying some of the behavior I saw in those I admired. I spent more time building relationships with co-workers, learning what motivated them, and sharing a little of myself in turn. I started trusting others a little more and let go of tasks and control of conversations I would have normally tried to hold tight to my chest.

I made conscious changes as well. I started asking for other people’s opinions more. Although it doesn’t come naturally to my personality, I started asking for help.

I started sharing more of my vision for the things I wanted to build and the changes I wanted to make. I worked to build consensus, soft-selling my ideas and compromising when necessary. I started letting others take ownership of my ideas as well.

And a curious thing began to happen. A lot of the things I was frustrated about and wanted to change — started changing.

Much to my surprise, it was entirely possible to lead and affect change among peers without any authority at all.

Also to my surprise and frustration, the hardest thing for me to do was also the most effective in getting others to follow my lead: asking for help.

It’s one of those head-slapping things that you feel dumb about when you realize how well it works on you, but when someone asks for your help (and really means it), it makes you feel important, which in turn, makes you want to help.

Asking for help is a little like rolling over and showing your soft underbelly. Some of us have a hard time doing it because of ego and vulnerability, but if you can get past that and have confidence in your end goals, asking for help is straight up magic.

You’re saying to the other person, “You, specifically you, have the power, skills, knowledge, etc… to help me accomplish this thing. You are important to our success. You are important to me.” That’s hard to turn away from.

If this sounds a little like manipulation, it absolutely can be, but that’s fairly transparent when it happens. I think most people can tell when someone else is buttering them up or asking for something just to mooch.

If you ask for help and can get past yourself to believe that you really do need the other person’s help, you and all the others you’re leading will be able to build spaceships and cure diseases. You’ll be tapping into the real social network, the type of collaboration that got humans out of scraping by, living in caves, and into planting wheat and building cities.

Control is an illusion

I am a control freak and used to be much worse than I am now.

I thought I needed control for things to be the way I wanted them to be. I thought I needed control to change things and didn’t really change much because also I thought I needed someone else to provide me with that control.

Seeking out control is a good way to make yourself unhappy, because you’re never going to get it and those that think they do have control tend to look like idiots to everyone around them (see teenage fast food manager above).

It’s hard to admit you don’t have control. It’s really scary too. That anything can happen at any time and you can’t really do anything about it is a good way to give yourself nightmares.

But it’s the truth. The most we have control of is ourselves and how we react to things, and even that’s limited.

You can get mad and yell and try to change someone’s mind about something, but you can’t control what they think. Nevermind that desiring that type of control is borderline psychopathic.

You can buy insurance and build your house into a fortress, but you can’t stop the freak electrical fire from burning it down while you’re out of town.

The best you can do is manage your reactions and maybe give a nudge here and there. That seems to be true for both leadership and life in general.

You don’t need control or authority to lead, because those aren’t real things. Instead what you need is empathy, vision, and a realistic understanding of what you can and cannot influence to direct your efforts.

We seek out control because it feels like an easy fix. We just need that promotion, or to be our own boss and then everything will be better. Control gives us the authority to lead the charge and get stuff done.

That’s just not how life works. Actual leadership is hard because having empathy, vision, and a detachment from control is hard. The sooner you give up chasing after control and put your efforts into building those other muscles, the sooner you’ll actually accomplish something.

Originally posted on

Learning People Tech

Do’s and Don’ts For Writing Online

If you were to ask me for one thing to do to advance your career, my answer would be: write.

Even if no one ever reads what you write, it’s worth it. Writing helps you think things through and work out problems, both personally and professionally. Over time, it also makes you a better communicator, more able to get your ideas onto the table and acted upon.

Putting your writing online helps you connect with people. It drives conversations that make you think and revisit your assumptions. If you establish a unique voice and present solid ideas, it’s also a really good way to market yourself.

Ultimately, I think that writing makes you a better person, someone who is more self-aware and able to empathize with others.

I’ve been writing online off and on for more than fifteen years, working as a freelance copywriter for some of that time. Here are a few things I’ve learned along the way that I try to improve upon every time I write.


Write like you talk. The world is clogged with overly formal academic- and corporate-speak. Formality and circular language put a wall up between you and the reader. Peppering in $10 words when 2 cent words work just fine doesn’t make you look smarter . It makes you look like a blow-hard who isn’t worth listening to and shouldn’t be trusted.  Here’s an example:

If, for a while, the ruse of desire is calculable for the uses of discipline soon the repetition of guilt, justification, pseudo-scientific theories, superstition, spurious authorities, and classifications can be seen as the desperate effort to “normalize” formally the disturbance of a discourse of splitting that violates the rational, enlightened claims of its enunciatory modality. – Homi K. Bhabha via The Bad Writing Contest

If you can figure out what Mr. Bhabha is trying to get across, you are smarter and more patient to me. I made it to “ruse of desire” before I started zoning out. It could be that he is saying something really profound, but no one will ever know because he wanted to be smart and fancy more than he wanted to express his idea.

There are times to jump into the deep end of English to pull out words that are beautiful and complex, but hammering people over the head with your word choices tends to dull your message.

Be clear and concise. I’m not advocating that you dumb things down, only that you need to be clear in what you express. Even if you use simple language, you can write a maze that’s difficult for people to follow.

Read some Ernest Hemingway, then read Charles Dickens. It depends on the subject and your personal voice, but using the razor-sharpness of Hemingway’s short, direct sentences often conveys more information than Dickens-style paragraphs.

Start simple, cut your ideas to the bone, then add meat if needed. Everything else is dead weight that gets in the way of understanding. You may end up at Dickens if that’s what’s needed to get your idea across, but start with Hemingway.

It was the best of times, it was the worst of times, it was the age of wisdom, it was the age of foolishness, it was the epoch of belief, it was the epoch of incredulity, it was the season of Light, it was the season of Darkness, it was the spring of hope, it was the winter of despair, we had everything before us, we had nothing before us, we were all going direct to Heaven, we were all going direct the other way – in short, the period was so far like the present period, that some of its noisiest authorities insisted on its being received, for good or for evil, in the superlative degree of comparison only. – Charles Dickens


Sometimes things are good and bad at the same time, and that can be confusing. – Me

Be honest. This doesn’t just mean “tell the truth.” It also means “be yourself.” The closer you can get to “yourself”, the more compelling your writing will be.  It’s scary to be honest, because you start expressing things that matter to you and make you feel (and look) vulnerable.

If you’re angry, happy, sad, or scared, express it. If you’re uncertain, even better.  It doesn’t matter if you’re journaling or writing professionally, let the doors open, even if it’s just a little. That’s not an excuse to rant or gush. It’s more effective to focus those emotions into surgical strikes that support the truth you’re telling without overwhelming it.

Showing that you are human creates a connection that helps people care about you and your writing. No one likes showing off their soft underbelly, but if you want an audience that cares, you’ve got to give them something.

Why else are songs about broken hearts so popular?

Admit when you are wrong. I screw up all the time. Last week I screwed up by not attributing a cartoon I used in a blog post to the artist. A couple of people called me on it. At first I was a little annoyed by being called out, but then I took a breath and said “You’re right. I screwed up.” and took the image down.

People often bring up angles I haven’t thought about in my arguments. I do my best to fold their feedback into my thought process and change course when needed. Sometimes that means retracting things I’ve written.

I do this for two reasons:

  1. I care about figuring out the truth of things more than “being right”.
  2. It’s more embarrassing to me to puff up and be dishonest than it is to say “I was wrong”.

The muscle you have to exercise in this is learning to let go of your ideas, both during and after you write. I don’t know how many times I’ve started writing something with a conclusion in mind only to do a 180 once I get a few paragraphs in – thinking the idea through and putting myself inside of the counter-argument forces me to let go of my idea and take hold of a new one.


Tie success to page views. The truth is, for every post you publish that gets thousands of readers, you’ll probably have written millions of words that almost no one read or responded to. Sometimes it feels a bit like shouting into a bottomless pit and it’s easy to get discouraged when you never hear an echo.

Even if no one is reading, keep writing. Write and write and write and write. Get comfortable with the idea that you may never have readers and learn to write for the sake of writing. The point when you stop caring is often the same point when you start getting readers. It just works out that way.

From time to time, go back and read your past writing. If you’re embarrassed by it, keep writing, because it means you’re improving. If you’re not at least slightly embarrassed by or frustrated with it, it’s probably OK to stop writing, because something is wrong – you’re either an egomaniac or you’re not getting better.

Forget to read. If you want to write well, you need to read. Immersing yourself in other people’s’ writing will help you identify strengths and weaknesses in your own writing.

Don’t limit yourself to a particular genre or type. Fiction, non-fiction, long-form, short, sci-fi and the classics – it all helps give you perspective and broadens your knowledge of what is possible.

Books about writing should be read with caution as they tend to steer people down rabbit trails where they spend all their time reading about writing instead of writing. There’s a danger in getting trapped in a search for “the secret” that will unlock your writing magic. However, used sparingly, some books about writing can be really helpful.

Here are a few that have helped me:

Be afraid to have an opinion. Take a stand. Don’t be so worried about people disagreeing with you that what you write is watered down, boring, and sounds exactly like everyone else. Why bother if you’re going to play it safe and generic?

People will disagree with you. That’s OK. If you’re writing stuff that no one would disagree with, it’s probably not very interesting.

One of the benefits of these disagreements is that they help you figure out who your audience isn’t. Something to keep in mind as well is that people who disagree with you are much more likely to respond than those who agree, so the negative voices will almost always outweigh the positive. If you need proof of this, look at Yelp.

There are people you will never be able to please, and you shouldn’t try to. It’s wasted effort. It’s OK to consider other people’s opinions, but focus your energy on the people who like your writing. In Seth Godin terms, those people are your tribe. Lead them.

You may be worried about turning off potential employers with your opinions, but consider this: if you have to hide who you are to work for someone, do you really want to work for them? If your views are polarizing, it may be a good idea to temper them a little, but if they are fundamental to who you are, you’re going to be miserable working for someone who would judge you for them.

Lastly, don’t feed the trolls. 

Some people will go past disagreement and try to drag you down with insults. It’s not worth engaging with them. Roll your eyes and move on. They just want a reaction and are starved for attention. Don’t give it to them.

Photo credit: Fredrik Rubensson

People Tech

Oklahoma City will never be a tech hub


When people talk about tech communities, they tend to have the coasts in mind – Silicon Valley, Seattle, Boston, Brooklyn. Few cities in the middle of the country stand tall as pillars of tech – Austin, Dallas/Fort Worth, and increasingly Kansas City and Omaha being the exceptions.

I know a lot of people who want Oklahoma City to join that club, to be a place where startups prosper and talent gravitates towards. It’s something I want too.

But, given current conditions, Oklahoma City will never be a serious tech hub, because Oklahoma City is in Oklahoma.

“What are these ‘priorities’ you speak of?”

While Oklahoma’s infrastructure decays and our schools are being shut down due to lack of funding, our legislature is busy moralizing and drafting reactionary, idiotic laws that anyone with even a middle schooler’s understanding of constitutional law would immediately recognize as indefensible.

Bridges and roads are literally falling apart. Schools are closing and already underpaid teachers are being laid off in a system that is 48th in the nation. Mental health services and poverty assistance have been completely gutted.

Core services are in a death spiral, yet the state legislature seems determined to spend all their time banging their heads against a wall instead of addressing actual problems. I’m not sure what litmus test they are using but it’s certainly not “Who does this help?” or “What does this improve?” or “What problem does this solve?”

It’s a continual cycle of:

  1. Pass law
  2. Law challenged, millions of dollars wasted
  3. Law struck down
  4. Return to line 1

Whether you agree with the ideas behind each piece of legislation or not, it would be hard to argue that repeating the same process over and over and expecting a different result is a sane tactic.

Attracting tech talent

Building a strong tech community is at least partially about attracting and retaining talent. Oklahoma City is doing a decent job of that right now, but the state is failing miserably.

I’ve heard several people say that Oklahoma City is becoming the “Austin for tech people with families”, which I think misses the mark. Austin is “Austin for tech people with families.” Oklahoma City is turning into “Austin for people who don’t care about having nice things or their children getting a decent education.”

It doesn’t matter how much OKC progresses or improves when everything around it and connected to it is burning to the ground.


Look on Twitter and Reddit and you’ll find tech people anguishing over whether or not they should stay in Oklahoma. I’m faced with the same question, even more so now that I have a child. I wake up every day asking “Is it worth it?” and “Is there anything I can do to make this better?”

Unfortunately, the answer is increasingly, “no”.

I have family and friends here. My wife and I have built a life here. Neither of us really wants to move, but we also want the best for our son and the prospect of that being Oklahoma is dimming.

At this point, I honestly have no idea what to do. I vote. I write letters and make calls. I work within my sphere of influence to make things better, but it’s like chipping away at a boulder with a plastic fork. None of it seems to help and that’s both tiring and heartbreaking.

People Tech

Building a better salesperson

My first tech job was with a regional VAR (value added reseller). I started in phone support, then moved up to bench tech, then to field engineer – a path that increased my exposure to customers and the rest of the business with each move.

I liked the technical work and helping people with their problems, but as I began to notice the sales engine that was at work around me, I started to dread coming to work.

Over time my reaction to the projects the owner and salespeople would bring to me went from “Yes, I’m on it!”, to “Huh, this is kinda weird.”, to “WTF is wrong with you people!?”

I found myself having conversations like:

Me: “Yes, we could upgrade every part in the customer’s PC, but wouldn’t it be better and cheaper for them to just buy a new computer?”

Salesperson: “Just put in the upgrades. It’s a big sale.”

Owner: “Go to their office, install this drive, and setup backups for them.”

Me: “Umm, we’re selling this? It’s 3 years old and the box is covered in dust.”

Owner: “It’s what we have in stock.”

Me: “But these things are worth like a 100th of the price on this invoice.”

Owner: “They don’t know that.”

Salesperson: “Can you look over this bid for these school lab computers?”

Me: “Why are you putting $1000 video conferencing codec cards in them?”

Salesperson: “Because we already have them and the grant allows it.”

By the end, I wanted to burn the building down with everyone locked inside. At the time I thought my experience was unique, that my employer was just particularly evil.

That was, of course, stupid. I was new to the workforce and naïve. Working for that VAR gave me the first insight into a cancer that is easily spread into any sales org.

Cracks in the system

Sales is an important job and I have met some amazing salespeople who are both good at their job and good at being decent humans. But sales is usually a pay for performance role which has inherent flaws, at least in the way it’s structured for most companies.

Quota-driven motivation tends to isolate the salespeople on a team and can lead to acts of desperation. Even some team-based quota models drive a culture of “every man for himself” that can never end well.

Traditional quotas recreate the cutthroat conditions of a medieval bazaar and living day-to-day in a system of “I must sell five more goats or my family will starve.” has an effect on the morality and judgement of an individual. How can it not?

I feel sympathy for people stuck in this situation. They have mortgages, kids to feed, whatever else and they feel like they don’t have the convenience of always fighting to do the right thing. It’s a crummy place to be – to have a moral compass and not be allowed to follow it.

In general, I find performance-based compensation off-putting.”You sell more, you make more.” makes sense and works pretty well on a small-scale, but crank it up to multi-million-dollar-mania levels and you’ve self-selected for a certain psychology.

The worst of humanity reveals itself when you put a bunch of people in a room who tie their level of effort to how much money they make. Extrinsic motivation is the stuff of pyramid scheme tycoons, politicians, and serial killers.

The status quo is ugly

On the customer side, I have multiple conversations a week that go a little like this:

Me: “In detail, here is the problem I am trying to solve. Could your widget help fix that problem?”

Salesperson: “Yes!”

Me: “So your product can cure cancer, solve world hunger, and keep our network free of viruses?”

Salesperson: “Yes!”

Me: “Do you understand anything that I’ve said?”

Salesperson: “No.”

Me: “And you still think your widget is the right solution for me?”

Salesperson: “Yes! It’s what I’m getting the highest comp on this quarter.”

I can’t express how frustrating this is and how much this sucks, especially when the person has swaggered in presenting themselves as a trusted advisor.

Customers need honest answers and guidance. They need help, even if it’s in the form of “Hey, I don’t think our product is a good fit for this problem.”

If you’re a salesperson who wants to build trust and a long-term pipeline that practically vomits money, be willing to walk away from a sale that doesn’t make sense. Spouting half-truths and outright lies may work in the short-term, but it’s a clichéd path that leads to gold chains, cocaine addictions, damaged relationships, and early heart attacks.

Personally, I respect the heck out of salespeople who tell me “no” and “I don’t know.” I will go out of my way to seek them out for future projects even if what they’re selling costs double the competition. I’ll come back to them when they change jobs and do my best to always take their calls.

A better path (maybe)

Being honest in sales requires a company culture that allows the person to be honest. The dude-bro, hyper-competitive environment that many companies create for their salespeople is not that. Quotas don’t support that, neither does performance pay. All those things box salespeople in and make them feel as if they have to lie, cheat, and steal to keep their job.

How about this:

  • Pay salespeople a good, fixed salary based on their skill and experience.
  • Get rid of sales quotas and replace them with other metrics like customer satisfaction and product usage. These are imperfect measures as well, but have a longer-term focus.
  • Manage salespeople like everyone else. If there’s a performance problem, coach and support them. If that doesn’t work, help them move on to something else.
  • Hire people who are motivated to do a good job because it’s the right thing to do, not because they want/need to chase carrots.

What about the salespeople who need the carrot? The ones who love the game, and are going to shuck and jive even when they don’t have to.

Honestly, eff those people. That’s not a personality trait that helps move humanity forward or builds a solid foundation for a business. If they can’t adapt to a healthier culture, they can go pound sand.


People Tech

Stop asking tech people to build your ideas

Sometimes people bring me ideas.

They say “I have this great idea for an app.” or “I have an idea for a tech business.” Inevitably, both are followed by “…and I just need you to build it for me.”

This is nothing special about me – it happens to most tech people.

I used to gracefully dodge with self deprecation or whatever else I could use to let the person down easy. In most cases I was being completely honest. IT is broad and few people realize just how broad and how many different technology skill sets there are.

“I just don’t know enough about that to be helpful. I’m not a developer, I do infrastructure.”

For the last couple of years I’ve started pushing back more, either by destroying the person’s idea or by encouraging them to take action on it on their own.

“You’ve just described Facebook. No, no…stop. Your idea is not different. It’s still Facebook even if you are calling it Gerbil Town. STOP!”

“You know what? That is a great idea. You should totally build that.”

Telling someone that they should act on their idea usually makes them a lot angrier than telling them their idea is terrible.

They say stuff like “That’s why I’m talking to you. I don’t know how to do this crap. I’m bringing this to you as a favor.”

And there’s the crux. You aren’t doing anyone a favor by sharing your idea with them.

Your idea sucks because it’s just an idea.

What you’re really saying to the tech person is “I don’t believe in this enough to even attempt to figure it out on my own. I’m just the idea guy (i.e. useless) and I want you to put in the effort that I’m not willing to put in.”

Learning to code (and most tech stuff) isn’t hard. Developers/engineers/etc aren’t (generally) genius wizards, they just put in the work to learn a skill.

It’s actually easier to learn to code than it’s ever been and there are tons of great training resources like Code Academy and Udemy to help. Like most things, it’s mostly a question of dedicating time and effort – and you don’t have to become an expert, you just have to achieve “good enough” to get started.

If you’re truly passionate about your idea, you’ll make the time and put in the effort.

If you’re asking someone else to do it for you, that’s a pretty good sign that your heart really isn’t in it as much as you think it is. Ponder that. Is it fair to ask someone to be excited about an idea you’re not 100% committed to?

There are people who have pulled themselves out of literally sleeping in trash-filled gutters to 1.) learn to read, 2.) learn to use a computer, and 3.) learn to code and build their idea. And here you are, having just asked someone to commit their energy to something “kinda neat” you thought about while sitting on the toilet.

Even if you find someone willing to put in the work to build your idea (and it’s usually some idiot kid or well-meaning novice), you’ll own something that you don’t understand. Good luck with that.

Too scared to start

Maybe you really do want to do something, but you’re scared. You think “I’ll never be able to figure this stuff out.” or “What if I fail?”

  1. Shut up and start learning. It’s just work.
  2. So what? No one is going to die if you try to make your thing and it doesn’t work out. That’s a pretty good safety net.

Tech people have the exact same fears. We worry that we can’t figure out the business stuff or the biology stuff or the construction stuff, or whatever discipline we want to work with. Most of us don’t execute on our ideas either.

We all say “if only…” and stop.

I’m speaking as much to myself as I am anyone else. I constantly have to kick myself in the butt and say “Stop being stupid. Do the thing.” – Every day of my life.

If you build it they’re at least more likely to come

Great ideas and terrible ideas are of equal value until they are real. The value is in action.

Go do the thing. Build it, even if it starts out crappy. Just by existing it is infinitely better than the thing you never built.

You may discover on your own that your idea is terrible. Good for you. You learned something you can take into your next project. If it turns out to be a good idea and you put in the work to shape the skeleton of it, you won’t have to ask for help, because people will swarm to you.

Stop asking other people to build your dreams. Do it yourself.

Image credit: Tsahi Levent-Levi


The opposite of Hunter S. Thompson’s Las Vegas

I haven’t been outside in three days. The hotel maze has continually redirected us back into the hotel. We went outside earlier in the week to try and find food but were steered back inside without realizing it. It’s easier to stay inside, so we do.

I have no interest in gambling or shows or anything else on The Strip. The rest of Las Vegas doesn’t hold any appeal either. Outside of a couple state parks close by and a sprinkling of jarringly green golf courses, it’s an urban wasteland.  Vegas is a glowing, cancerous growth upon an otherwise pristine desert.

Lobbying by the local taxi cartel meant that we could not grab an Uber or Lyft car when we arrived at the airport.  Instead, we were directed into the cattle shoot of the taxi line and herded along until a taxi was available. Moo… Moo… Move along.

I’m sure some taxi lobbyist somewhere was simultaneously arguing about the superior customer experience of their business.

Check in, get an upgraded room, then off for food. Google Maps reveals that my favorite Vegas taco shop has closed its location on The Strip. Is nothing sacred? It was the only Vegas thing I was looking forward to.

We find an alternative nearby that is decent but overpriced and poorly served. It does provide a good opportunity for conversation and people watching though. Drunks at the bar shout at the football game on TV. One of them throws his hat is disapproval.

I poke and prod my travel companion with questions. I want to know who he is and what we have in common. I’m impressed by his ability to redirect when I touch a nerve or he senses controversy nearby. I am certain that we disagree on many things, but he seems disinclined to embrace ideological extremes. That’s all the common base that any two people need.

Later in the week, I’m put further at ease when he asks me “Who’s Ayn Rand?” after I mention seeing one of her books in the window of a casino bookstore.

“A selfish hypocrite.”

We are in town for a convention that seems close to overflowing the walls of the Sands Expo. The subject matter is interesting, but the food is terrible and every room is uncomfortably packed. They open the show floor for two hours on the eve of the convention for a reception and navigating the clogged mass of humanity slowly rolling through the room borders on frightening.

The me of ten years ago would have abandoned ship after looking into the room or otherwise collapsed in a ball of anxiety and claustrophobia.

I have the advantage of height and can see above the crowd, but struggle to not trample on the shorter people around me. Keep moving and get out of the way.

We settle into a cycle of vendor meetings, eating, walking the show floor, and catching up on work. The day/night cycling of artificial light and sky-frescoed ceilings merge the days together. We are relieved when we discover a route from our hotel rooms to the convention space that circumvents the gaming floor, which is filled with cigarette smoke, sadness, and an ignorance of statistical probability.

In the evenings I stare out my hotel window and work on a presentation I’m supposed to give at the next convention I’m scheduled to attend. Unfortunately, that means I’ll be back in Vegas in three weeks.