Dropping Up: A Life in Tech Without a Degree

I never went to college. I wish I could say that it was entirely intentional, that I knew exactly what I was going to do after I graduated and followed that plan, but that isn’t how it happened. The real story is a lot less romantic. For those thinking about switching careers, or standing at the threshold of ‘real life’ and unsure what to do, it might hold some lessons, so let’s get started…

What really happened was that I was exhausted by school, terrible at working on things that didn’t have an immediate impact, and didn’t really get how the college application thing worked. My family has never been big on debt, and with the grades I had (from being terrible at things that didn’t have an immediate impact, like homework), I certainly wasn’t getting a free ride. I wanted a break, I wanted a chance to do real, practical things. The only problem was that I didn’t know what those real things were, and didn’t know anyone doing them.

Find an Open Door

In 1995 when I graduated high school the most exciting things were happening on the Internet. I’d learned a little HTML after getting online in 1994, but the web was still very much a “We’re trying to figure things out” space. Spaces like this are great, because even if you don’t have tons of experience, there isn’t a huge pool of best practices already to get up to speed on. I connected with some folks who were starting an Internet Service Provider in late 1995. This connection was something of a fluke, someone I knew from church. These days there are much better networking options for technology, but never turn down an opportunity.

Fortunately I had some useful knowledge about how to get MacOS machines online. It wasn’t a lot, but along with the HTML skills it got me in the door. These days the equivalent of that knowledge might be Photoshop skills from making LOLcat gifs, video editing skills from making meme mashups, some hardware skills due to school MindStorms programming, linux administration from running a Minecraft server, or social marketing skills from running a popular Twitter account, Tumblr blog or Facebook page. Anything that’s hard to master in a few days can get you in.

Don’t Expect it to Pay

When I first started doing Mac tech support for that little ISP in San Marcos I made a little over $200 a month. That isn’t much money, but it put gas in the car and put me in a position where I could play with the toys. Your job, once you have toys to play with, is to play the heck out of them.

In the first 6 months after I got my ‘job’ at the ISP, I built them a web site (you can still see it here) setup San Marcos’s first quake server, created Austin’s first streaming radio station (I registered mix947.com in February of 1996, and got the streaming working with a demo license of Real Media Server for BSDI and an old shop boombox), created a weekly user newsletter, started weekly user meetups at the shop, and even got involved with the local Internet Users Group at the library (which I ended up running).

You only do those kind of things if you’re in a space where there are no conventions or expectations. When there aren’t any streaming audio stations, setting one up with a 5 stream limit isn’t a deal-breaker. When all your users are early adopters you don’t need a marketing expert to write a user group email. You just do it. Luckily the ISP was run by Chad Neff, a great artist and stalwart defender of the user. He encouraged me to try things, and was my first great mentor in technology.

Hold on Passionately, but Loosely

An early, hard lesson to learn is when to let go. I didn’t let go of that job well, and though there were extenuating circumstances, and more people than just me were caught up in it, it made my life really messy for a few years. When you’re in the middle of the job, fight for the users as hard and as passionately as you can. If you aren’t creating things for someone, it’s a waste. Whether you’re knitting hats or writing tweets, you’re doing it for someone. Strive to make them as happy as possible.

Conversely, you have to know when it’s time to go. All things come to an end, and being able to sense that end and depart gracefully is a skill. Learn it. If you’re going into tech, read founder stories, especially the stories from founders who get kicked out. There’s a shift at each phase of a project or company life-cycle, from startup to growth and growth to long-term maturity. Finding out which phase you fit into best is important, as is being able to sense when that shift is coming.

Aside: Do you like to experiment, throw things together and see what sticks, with little heed for long term consequences? You’re probably startup minded. Do you like some stability, but enjoy seeing success build, working long nights to land the next client? Maybe growth is your bag. Are you risk-averse? Do you like long-term stability, dependable processes and maybe even enjoy corporate politics and intrigue? Then maybe you want a project in its mature phase.

Also, strive to recognize when things are heading for the toilet. There’s some honor in being the last one to turn off the lights and lock the door, and I’ve done it more than once, but it’s rarely the best thing for a career. Try and step back once in a while and assess things from the outside. Get some opinions from people you trust. Do right by your users, but recognize that not every situation is salvageable.

It’ll Be Embarrassing

For a long time I had a vision for starting a web design firm like Vivid Studios, a bay area web design shop that had the mid-90’s Wired techno-punk aesthetic nailed. It was a techno rebellious company producing amazingly creative, cutting edge work for great clients, and I wanted to be just like that. Unfortunately I was in San Marcos, Texas, not San Francisco, California, and I didn’t know anything about running a business, much less a hip design business. I didn’t know Bauhaus from an outhouse, if you know what I mean.

I carried that dream around for a lot of years, wanting to belong in a group of smart, forward thinking creatives. The dream took a lot of different shapes, and matured as I did. The first attempts were… laughable. In 1997 I started doing business as 57th Street Productions (yes, we apparently offered ‘innovative thinking’ as a service), which in 1999 became 57th Street, Inc. 57th Street lasted a year and a half before ceasing to be.

Aside: A while ago I’d read something that said you can find a lot out about a person by how they view their youthful mistakes. People who think ‘look at me, I was so stupid’ versus people who think ‘look at me, I was so cute’. People who realize that youth and inexperience is a perfectly valid excuse for shortcomings are more likely to grow and be happy than people who judge themselves harshly. Don’t be down on your past. Everyone has been the fool. Don’t settle for that being the whole story, though.

When you read stories about Bill Gates or other tech luminaries starting companies in their 20’s and being wildly successful, what you don’t read is about the support networks they had that made it possible. You don’t hear about the people they knew who had business experience, the years they’d had access to computers in their teens, the contracts they’d gotten due to flukes. When you don’t know how to get from point A to point B in business, don’t assume you can just muddle through. Go out and read some business books. Realize that if you don’t know people who need your services/product/etc, you can’t make money. Realize that if you only have one of these clients and don’t have any way to find a second, your business isn’t really a business, it’s just a relationship. Go find people who run real businesses, and get them to teach you the ropes. Ask them how they find clients, especially if they’re in a business similar to yours (say, physical engineering services to technology consulting). If you can’t sell your product for more than it costs to make, again, no business. You don’t need an MBA, but you need to know how to balance a checkbook, forecast earnings, pitch a client, close a deal, and make a profit.

I ended up doing some things I’m not really proud of at 57th Street in the hope of forcing that Vivid Studios dream into reality. I made some bad decisions (hiring people for personal reasons, not diversifying the client base, not making enough connections), and the only reason we made it as long as we did was that it was hard not to make money in technology in the late 90’s. If you’d like to get a taste for my embarrassing phase, you can check out these two tours, one from my ISP days at itouch.net, and one from my days as 57th Street, Inc.

You’ll Get a Break

What seems to happen is that eventually, if you keep plugging along, you’ll get a break. It will almost always be a result of some risk you’ve taken, or avenue you’ve explored. If you’re well connected, I guess it could be a connection your parents or buddies have, but that wasn’t my experience. In 1997, after joining The WELL, I met Jon Lebkowsky. We got into an online discussion about FreeNets, something I was interested in from my connection with the San Marcos Internet Users Group, and ended up having lunch at the Waterloo Ice House. We ate at the Ice House because it was next door to Jon’s gig at the time, Internet Guy at Whole Foods Market.

Nearly everything that has happened since, I can trace back to meeting Jon. Jon was having some trouble with Whole Foods in-store kiosk system. They were Windows NT Workstation based PCs with touch screens that browsed an internal web site in a locked-down browser. They were always breaking, stores shipped them back to WFM Central, and they had to be fixed. Jon needed someone to do the fixing, and I took the job. Your break may not be glorious. For me it was a windowless room fixing and re-imaging Windows NT machines, but it was a foot in the door at a company that had real enterprise-level problems, and even better, I got in at a very unique time.

Don’t Be Afraid to Go Up

My time at Whole Foods, in retrospect, was very strange. I’m sure some people have had similar experiences in other places, but now that I look back on it, it was kind of crazy. I think, though my memory is a little foggy, when I started working contract for Jon on the kiosk project I was making about $15/hour doing run-of-the-mill PC maintenance. Over the next 3 years my rate ended up peaking at something like $150/hour, and I was on a 40 hour a week retainer. Somewhere near the end the CIO of Whole Foods Market asked me into her office and offered me the chance to rebuild their programming team, hiring whoever I wanted. I was… 22. So, it’s a weird story.

I think my experience at Whole Foods comes down to two things. One, the luck to be in the right place at the right time, and two, never saying no to a problem. When I started on the kiosk project I was just re-imaging systems, fixing ones that were broken, and shipping out the replacements. That’s $15/hour work. Eventually the vendor that was supplying our keyblock software (so you couldn’t get out of the browser and break the machine) disappeared, so I offered to write a new one. I’d never written Windows NT device drivers before (or really any C code), but you don’t know you can’t till you try. Once you’re maintaining source code you’ve suddenly become more than an IT tech, and I think my rate bumped to $35/hour.

Now comes the right place/right time side of the story. This was in 1998. The Internet was hot, E-Commerce was boiling hot, and all the sharp programmers who’d toiled away for years on awk scripts and maintenance software wanted to go do the hot new thing. Whole Foods Market started WholeFoods.com, and nearly all the programmers from inside of Whole Foods left to join it. This left a gaping hole in the company that was being filled by one person.

Simultaneous to this exodus I, too, was exploring the job opportunities at WholeFoods.com. They made me an offer for $35k a year, and after verbally accepting it, I drove over to Whole Foods to get some dinner. In the parking lot I ran into Mark Mills, that one guy holding closed the gaping hole in internal development. While swinging around a pole in the parking lot, Mark gave me my next big break. Come to work for me, he said, and I’ll pay you $85/hour contract full time. You don’t have to be great at math to know that’s a lot better than $35k/year, so I declined WholeFoods.com’s offer, and went to work for Mark. Sometimes the opportunities are obvious.

You Have Potential in Others Eyes

When I joined Mark on the programming team, I was not a great programmer. I wasn’t even an ok programmer, but Mark, like Jon and Chad, must have seen potential, so he gave me problems to solve, and let me solve them. He gave me advice, showed me some tricks, and let me do things how I needed to do them. Mentors like this are great, seek them out, cleave to them, and strive to be like that when you’re in a position of authority.

After a few months of building data exports, Mark left Whole Foods as well. And then there was one.

Again, this is a right place, right time story. I had web skills, sys-admin skills, network skills and programming skills, and was in a large company with no internal programmers. Over the next few years I was able to build a suite of web applications (job posting, CMS, inventory management, document management, etc), working directly with the teams who would be using them, without any real technical oversight. I like to think that I did a good job, but I suppose that isn’t for me to judge. I just know that they were still using some of those applications years later, and the people I worked with always seemed happy to see me.

Once you get an opportunity to work on projects, it’s a chance to prove yourself and get experience shipping real product. During this phase I never had a project cancelled, I always delivered them on time, and I supported them myself. Strive to be the best, work professionally, and treat your users and customers how you’d want to be treated. You’ll make mistakes (always compress uploaded documents in a document storage system, your network storage admins will thank you later), but you learn from them.

Surprisingly, during this phase I even got called back in to WholeFoods.com (and later WholePeople.com) by Jon to build some integration software with Yahoo! Store, and managed to deliver in a few weeks what another consulting firm said wasn’t possible. This is your ‘don’t know it isn’t possible’ phase, enjoy it. Work your butt off, learn as much as you can, try new things. Responsibility comes next, and it’s a bear.

Out of the Garden

Eventually the gravy train ends. Whole Foods Market’s CIO offered me the job as lead developer, and the opportunity to hire anyone I wanted to rebuild the programming team. My life would have been completely different if I’d accepted, but I couldn’t in good conscience. I was 22. I didn’t really know what I was doing, but I knew I didn’t know what I was doing. I didn’t really want an employee gig. I turned her down.

The next few years heralded the popping of the dot-com bubble. I drifted away from Whole Foods Market as they hired programmers internally, though I kept maintaining the systems that ran the WholeFoodsMarket.com web site until they replaced the entire thing in the late 2008. From the time we launched it (on time) in 2000 to 2008, it was powered by the same Apache Server-Side Include based architecture, running on a single Sun machine.

After WholePeople.com imploded with the dot-com bubble, Jon Lebkowsky and I started talking about starting a web consulting company. Visions of Vivid Studios started dancing in my head. I even managed to rope my buddy Matt Sanders into joining us. Together we founded Polycot Consulting, and started learning all those business lessons the hard way.

Remember how I said that a business with only one customer and no way to find more isn’t a business? That was us at Polycot. We spent a lot of time in the wilderness, trying to find work in the post-dot-com rubble. It wasn’t easy. We learned a lot of lessons the hard way. A few of them:

• You can’t pay your rent with leads, you can only pay your rent with paid invoices.
• There’s a difference between the things you want to get the job done and the things you need to get the job done.
• Doing cheap jobs for ‘exposure’ is a trap. You will end up just doing cheap jobs, and your customers will expect the world.  Our CPA once told us that Pro Bono work was a great way to get other work, but the other work will always be Pro Bono.
• Corporations view the world differently than non-profits and mom-and-pops. Don’t ask a Fortune 500 if they want to pay $100 extra for a life-time license of some software you’re using, that isn’t real money to them.
• You need someone who knows how to sell. You can evangelize a product, but you have to sell consulting.
• Make a product, and make sure that everyone’s willing to put the time into it. Better yet, make a bunch of products. When you’re scraping by on hourly work it’s easy to say ‘this doesn’t pay, I’m not going to do it’, but look at it this way: Each of those products is a learning opportunity, and in consulting, if you don’t learn you die. One might even make some money.
• Evangelize your successes. Write up each project that you do. Publicize the heck out of it. If you did something awesome and no one knows, it doesn’t matter.
• Recurring income is what keeps consulting businesses afloat. Just because you, as a scrappy developer, think that support contracts are a ripoff doesn’t mean they are, and if they didn’t exist, most of the things you like wouldn’t, either.
• Running a business is crazy hard, most of them fail, if yours doesn’t, good for you, but be open to the possibility that it should have.
• Realize that you could very well be doing work in technology for the rest of your life. Take every opportunity to learn a new thing. The more you know, the more valuable you are, and in the end…
• You are your product.

The Soft, Cozy Womb of Corporate Life

One upside to doing a bunch of projects for a bunch of people is that we met a bunch of other technology people. I did a few projects for Mitch Kapor (of Lotus fame), we had Matt Mullenweg in our office before WordPress got huge, I worked with the guy who designed Google+ on a project, and some guys we worked with are behind SB Nation, The Verge and Polygon. Once you meet smart people and show them you’re a decent sort of person, other doors start to open. These doors are sometimes soft, inviting, and open onto worlds of bureaucracy and 401k plans.

One of the last projects we did at Polycot before the founders went their separate ways was MindBites. MindBites is a video commerce platform, and after we built the prototype, we migrated the customer to a company called Squeejee for ongoing development work. A few years later, some folks from Squeejee would end up at Hewlett-Packard, brought in to spearhead HP’s push into the public cloud space. They would bring on Matt Sanders, and thanks to the good impression I apparently made, me.

I’ve been at HP for two and a half years, and I’m finding that a lot of the lessons I learned earlier still stand. Namely:

• Look for a space where people believe in forgiveness over permission. Then do what you feel needs to be done.
• Look for smart people and learn from them. Communicate. Converse. Network, even if it’s hard.
• The people above you want solutions, so when you’re presented with a problem, come up with one, and do it.
• People in the corporate world are used to passing the buck and bureaucracy They are impressed by responsibility and rapidly delivered solutions.
• Take credit when it’s due, share it when it should be, make sure contributions aren’t overlooked.
• Don’t let yourself get stuck. Corporate life can be a trap. A slow moving, slow progressing trap. Always be on the lookout for the next spot, the way to gracefully exit, the new problem. This counts double if you’re a startup phase person.
• Many (most?) corporate projects get the axe eventually, some before they even ship. Don’t take it personally. Try to lead the inevitable downturn. Play from a position of innovation. If they want to kill it, be the person proposing the exciting new possibility.
• Take every opportunity the company offers to learn, present, meet, train, etc. Just because you got a job doesn’t mean you get to stop hustling. Again, the cardinal rule is…
• You are still your product.

Fill in the Gaps

One thing I’ve come to realize, the longer I’ve worked in tech, is that the knowledge space is huge. Enormous. There’s no way to know everything. There are entire fields you haven’t heard of, entire ecosystems that have existed for years that you know nothing about. Your job in improving your product (yourself) is to fill in those gaps as much as you can. It’s better to be a generalist than a specialist. It’s better to know two programming languages than one, and better to know three than two, especially ones that compliment each other, like Python, Javascript and Go or Ruby, Javascript and Node.

If you’ve focused on the frontend, do some backend tutorials. If you’ve done HTML and CSS, try Drupal or Django or Rails. If you’ve done databases and integration projects, do some front end stuff. Look at jQuery. If you’ve done just web stuff try loading up a server, setting up backups, and installing software. If you’ve done server stuff, try creating some HTML5 Twitter mashups. If you’ve only done sites for a small set of users, go big, pull down some giant Twitter datasets and start playing with R and Hadoop. If you’ve used imperative scripting languages, try functional ones. If you’ve mainly done P-languages or Ruby, try Lua or Go or TCL or LISP. Write a compiler. Do some computer vision projects. Hack on Arduino or the Raspberry Pi. Write an Android app. Go outside your comfort zone.

As to how deep you get with these things, here’s an arbitrary rule of thumb I just made up: Learn enough that you could give a 45 minute talk about it. If you’re single, learn a major new thing every quarter. If you’re married, every 6 months. If you have kids, especially little ones, every year. Adjust as you see fit.

Above all, don’t beat yourself up if you find yourself behind some imaginary curve. If you’re 35 and only know Java, that’s fine. That’s great! There’s tons to learn, and it’s going to be crazy and exciting and you’re going to look at technology in an entirely different way. If you’re 50 and think you’d really enjoy this, there’s never been a better time to learn, and it’s never been easier to get from nothing to a working product. Try one thing. Pick one of these things that interests you, and spend a weekend on it, if you can. Commit to just getting one thing working. If you can relate it to your job and do it on company time, all the better. If you enjoy it, keep going.

Life Without College

So, I may have strayed from my original point about college. There’s a maxim I’ve heard that goes like this: Your degree gets you your first job, and after that it’s all about the work you’ve done. For people who don’t go to college, the trick is getting that first job, and filling in anything you may have missed by not going to school.

Look for under-saturated specialties. It isn’t a great time to get into small business web design. That ship has sailed to custom WordPress themes.  If the web really floats your boat, get into Drupal, but don’t stay there forever.  Technology moves, albeit sometimes slowly.  Mobile development was ripe a few years ago, but making a profit in it is really hard.  It’s a good skill to have, but a hard market to compete in.  Look at things like RubyMotion, to get your feet wet.  There are opportunities in DevOps (a fancy word for programmers who deploy their own code into production), big data, personal and business clouds, personal analytics, and integrated Internet enabled devices.  There are always jobs to be had in enterprise software.  Tech companies introduce software to solve new problems, so look at the announcements that are getting a lot of buzz.  CloudFoundry had a lot of buzz, and now Docker is really hot.

Getting your first job:

• Find something you feel excited about (programming, networks, server administration, HTML, design) and do a bunch of it. If you’re a lecture-learner, watch videos. If you need practical applications, ask people for ideas of projects. If you have collaboration skills, pair program.
• Meet people. Go to Meetups. Join online groups. Listen a lot. Don’t be afraid to ask questions. Follow the rabbit hole down. Don’t be afraid of not understanding. The pieces will fit with time. You have to practice, though. You have to actually write code, create graphics, code web pages.
• Share what you’ve learned. If you can teach it, maybe you’ve learned it.
• If you’re programming, share your code on GitHub. If you’re creating videos, post them to YouTube and Vimeo (I partied with those guys once, they’re cool, but New York-trendy).
• Ask for feedback, don’t expect it to be glowing. Don’t try and change everything, but internalize what you get. You’ve created something, don’t doubt yourself. The goal is to get better, not to be perfect.
• Talk at meetups with people from companies you respect. Look for open doors, even if they aren’t exactly what you want. Expect to do a lot of hard work that isn’t glamorous and isn’t fun. It’s better to do less fun work at a company you love than cutting edge work at a place you hate.
• Get some experience doing contract jobs, say, on oDesk. It will suck. You will hate it, but it will teach you about shipping code, supporting code, and dealing with clients.
• Technology managers rarely care about the jobs you’ve had, and almost never care about what school you went to. They care about the work you’ve done. When I’m hiring now, education is nearly irrelevant. How you spent 4 years as an immature post-20-something is nothing compared to how you spent the next 5 or 10. Google seems to agree. Google has teams where 14 percent of the folks never went to college… Google!
• Hierarchical academic environments still exist (HP Labs is really oriented that way, I’ve heard), and are probably places you want to avoid. Most places like this have a reputation for being so. If you ask around, you can probably get the skinny.
• If the opportunity appears, jump on it.

Once You’re In:

• Never turn down an opportunity to do something that excites you.
• Find a mentor, someone who shares your interests and has experience. Don’t go crazy with their time, but don’t underutilize them. People who’ve been around for a while want to share what they’ve learned, but they want you to show initiative.
• Find excited, cool people. If you’re in a corporate environment it can be easy to get depressed. Don’t be an antagonist. Be the person you want to hang out with. The future is wide-open and unknown. The present is temporary. Always be dreaming.
• Take advantage of learning resources and your newfound credibility.
• Watch for the phase changes. Be sure you’re where you’re most productive. Seek out managers who understand that personality fit, and strive to keep you there.
• If you get hired with no prior tech experience, you probably aren’t going to make much money. Work on your skill set, network, and realize that you may need to join a different company to work your way up the salary ladder quickly. Learn to negotiate salary. Google it. It’s important.

Once You’re an Old Hand:

• Share your knowledge.
• Protect those below you.  You’re experienced and have tough skin, sometimes they don’t.  They need to know the realities, but they may not need to know how the sausage gets made.
• Look for people who need mentors. Encourage them. Connect them with things you think will help them.
• Take the time to learn about the people you work with. Everyone has a story. Maybe they didn’t get a CS degree. Maybe they’ve had similar challenges. Maybe they have an amazing background or skill you knew nothing about.
• People come into technology with different skill sets There is no such thing as the complete programmer. Look for your own gaps and those in others, and figure out ways to fill them.
• Lead by example. Do good work, don’t be a jerk, and treat everyone with respect.

A Few Last Notes

If I’ve learned anything in the last 15 years of being in technology, it’s that patterns repeat. I’m sure there will be changes in the future. Once you have kids, your desire to really jump on those transitions may start to slow down, but in the end they’re what a career is about. I’ve been fortunate to meet some very smart people inside HP who’ve been there for 30 years or more. They started out on calculators and are now in cloud. Maybe I’ll start in the web and end up in synaptic AI. Maybe that’ll be at HP, maybe it’ll be somewhere else. There’s always something new to learn, and there’s always that product of ‘you’ to work on.

If anyone reading this is looking for specific advice, needs a mentor, or would like some feedback, let me know. A lot of very gracious people have given me a lot over the years, and I want to pay it forward.