I spent my teenage years building fan sites and social networking sites for games. I made enough money to pay off college, get a nice apartment by the water and have a couple k leftover come graduation.

I was curious why I wasn't getting a lot of hits on my resume, so I talked to a recruiter at a networking event who had seen my application (for one of the "unicorns") and she said they where uncomfortable with how entrepreneurial it looked.

I removed the sections from my resume, removed all of my contract work too - only listed the internships and found some other grads (that got jobs) resumes to copy the language style. Pretty much instantly my resume was getting me double or triple the interviews.

Bummer too, because I worked my ass off and always had the false impression that employers would like that.

Sometimes its the gap between marketing (how they want the company to appear) and HR I think. Marketing wants innovators, HR wants workhorses that move in a strait line and don't try new things.

That's odd. We get excited when we see an entrepreneurial profile like yours. We have several developers who want to start companies and actually try to help them along that path.

The benefit to a motivated engineer is you can give them problems to solve instead of specs. The outcome or results can be less predictable but can also be much more effective.

When I got out of contracting, and later after 2008 business failure, I lost count of interviews that went thus:

"You're perfect for the role", "You have just the skills we need", "you're by far the best of those interviewed"

but by email later, sometimes directly

"we think you'll get bored", "we think you'll leave after six months" etc

(Sometimes, "we think you're a bit overqualified")

For sanity's sake I went on a few contract interviews, and usually got an offer.

My experience was that employers are utterly terrified of someone who's got some entrepreneurial or business history. Sure the money was less, but there many reasons to want to go back to employment.

As they didn't like it, I always wondered why so many invited me to interview when the 5 years of successful business and 4 years of contracting was very clear to see on my resume.

I've had the same experience as the poster you're replying to. I had to remove any bits of the fact that I bootstrapped my own fledgling (small, successful in it's own right, yet not capable of sustaining full-time wages) startup from my resume to get interviews. I was told that my resume was "intimidating" and "sending the wrong signal" by friends who are developers whose input I trust.

But I completely agree with what you've said. I am a problem solver or a product engineer or whatever this skill set combination is being called these days. I pull from a wide range of experiences to solve problems and I'm not very happy when I have to work off of a rigorous spec.

Unfortunately, that doesn't mean much to most employers in my experience. I don't fit in to most places and most places don't know what to do with me. It's made for a rather frustrating career over the last decade but I simply don't know what else to do.

How do you feel about the potential for high turnover with entrepreneurial types, as it seems the general consensus is they will inevitably leave to start their own thing? How long do you expect someone to work for you before hiring them, getting them up to speed with your system, and integrating them into the company is a worthwhile investment?

When I get asked this in an interview, I always answer the same way: yes, I will probably go to the next gig faster than other employees. But I will get up to speed faster, and I will produce more output for the business itself in the time I'll spend in your company.

This is the reality but my question was more about perception vs reality.

When you leave, much of your knowledge about the thing you helped to build will leave with you. They want that to stick around.

Then pay for it. It's pretty much that simple.

It might be a question of commitment signaling. Some reviewers might ding candidates that seem to have a ton of work going on outside of work. Maybe even more so if they see a candidate hasn't held a job > a certain # of years before.

Not sure if HR thinks that deeply during resume review, though. If you're not getting past that screen it's probably just match-the-buzzwords-listed-in-posting density—more "filler" words (started awesome website, did amazing things) means less % matching words

Young engineer, I tried being entrepreneurial. I confirm team leads don't like it, even if the company displays the marketing you describe. Better become more skilled in your field than just overly motivated. It's sad that we only understand that after a few years in the job.

I had a similar background--worked my way through school doing small to medium size freelance projects. Much of my freelance work was contracting for one company (where I was mentored by one the senior developers) and few startups, so it wasn't quite as bad as what you experienced. Some employers think you're not "office material" if you happened to be a hard-working, independent worker that managed to pay their way through school while learning on the job. I assume I probably dodged a bullet working at any of those places, if that's the way they hire.

After graduation, I had a few tell companies me that my work during school as sort of a "black mark" and I think it's sort of humorous looking back at it now. Currently, I'm the technical lead for my dev team and the contract work I did while in school is probably the best experience I had for the work I do now. Gave me a broad range of experience that reinforced the theory and concepts I was learning while in school.

Interesting. Perhaps something I can learn from. What kind of companies have you worked for (large corps / startups / SMEs?) and what kind of work do you do for them (any specialisations)? How do these experiences contrast to your pre-employment/self-employment experiences?

I do full-stack development. Front-end, back-end, some server admin, DB, UX, SEO, etc.

I worked at a F500 building tools to visualize big data and had a great time. Learned a lot and had a lot of freedom.

Afterwards, a VC funded startup - didn't really fit in, most of my co-workers where hardcore academics and it had a lot of micromanaging.

Also did some contract gigs, subcontracting for another company which could be good, bad or neutral (all depends on the client).

Self-employement is awesome, because you get to explore a ton of new things. You get to learn about SEO, business models, cutting costs to increase profits, increasing conversions, brand image, UX, etc. You also get to know your audience really well.

In my case, the biggest downside is I could never build a strong network because most of my revenue was coming from ads and donations and the target audience was younger.

It's easier to network when you are out and about, and always working with people who have their own networks.

I'd love to start a company (on a bigger scale) some day, when I have a stronger network, a larger skillset, and some capital so I can make sure I am feeding myself every week :)

How did user testing go for the UX portion of your work?

Is HR the first line of contact when applying in most companies? Where I work I think we (the developers) get all the resumes that come in and decide to decline or continue the process, HR only handles the logistics

That's a sign that you have what it takes to start consulting on your own. Every client I've ever had has appreciated my non-programming skills. I've never taken a client until I thoroughly understood the business and I have rejected many potential clients because I did not agree with the business-end of the software need.

Specialization is indeed valuable but it's not a binary master-of-one vs jack-of-all market. I am A+ in a specific platform, A in a couple of market segments, B+ in a handful of valuable technologies, B in many professional skills, C+ in most business activities, and C in everything that I have never encountered before. I don't need to be A+ in everything I touch and I am definitely not just a C in every single trade.

You don't have to start a business or be lucky enough to head up a team at a large business to get a chance to apply your skills fully. I don't want to do either so I consult with small-to-mid-sized business and research+plan+code+test+train whatever they need. For someone on a W2, this seems unconventional and risky. Don't want to sugar-coat it - it is. But what it's not is unsatisfying.

If you are in a position in life to take a small risk on yourself, pick up a small consulting gig that is more than just pure coding/technical. The more you perform like a vendor and business partner and less like an hourly contract employee, the closer you get to applying your full range of skills.

I appreciate your perspective however right now, due to personal circumstances/ bureaucratic reasons, I need a full-time job. I have run my own businesses previously and enjoyed it immensely however they also burnt me out. I learnt a lot from this that I will take with me. My experiences since then have made me realise I should apply the approach from your 1st paragraph more in future.

No worries mate. Though notice I said consulting repeatedly and contrasted it with running a business or being employed. You can sell your services without having to run a business. I don't want to hire anyone, advertise, have an LLC/S-Corp to manage, deal with licensing, or even print business cards. I just want to show up, do the work, and get a check.

Like anything, it depends. If you don't like being a cog in a large machine, look to smaller shops. I hate working in large firms precisely because I'm bad at shutting up and being a cog.

And you know what? In big shops, painting outside of your lines actually can cause problems. Questioning decisions on things going on outside of one's domain causes slowdown (at the very least, wasted time in meetings where people explain why that stupid idea actually has to be that way, etc.) and frequently, conflict, because when the norm is "stay in your (metaphorical) cube", questioning decisions can all too easily look like an accusation of incompetence or as a power play.

Go where your other skills have value.

I think it depends on the job for which you're applying.

We want our senior developers to be willing to dig into business requirements and constraints without being asked to. Curiosity, orthogonal business knowledge, etc are important at that level and higher.

However, we've seen multiple times that the junior developers just can't do it with the rare exception. They have enough work getting up to speed on one or more of: the language, the large internal system, the large client systems, how the client works, how to be an employee, how to deliver value over the long term and not go 2 weeks with no delivery then 2 weeks with, etc.

You're right, sounds like maybe a bit of over-generalization from your situation :)

Do you have a direct manager who talks with you about your career growth? A good one might help you find projects that engage your broader interests. There are certainly roles and projects that involve some degree of inter disciplinary work, and not just at founder or team lead levels. If not at your company, there are certainly some at others. Startups especially welcome diverse contributions from early employees.

Hope you find a good outlet for your interests! If not in an engineering role, maybe try a side project.

I was always interested in technical PM roles, but I'm best at full-stack development. The most important work criteria for me, is to see the business as something I'd invest in. If I think the product matters (can have a serious positive impact on it's customers, rather than a marginal one), it's easy to get excited about it.

I have a few dev managers and experienced engineers who I've kept in contact with from an old summer gig - they all think I should join/create a startup.

I'm actually on the job market right now (Seattle) - but considering moving to CA because recruiters in that area seem to like me a lot more. Might be a culture thing.

I feel the same way, it's hard to care about something you wouldn't use or evangelise about, unless it's deeply niche and complicated enough to go over my head and make me feel dumb.

Well it looks like you got a positive signal from Instacart :) Good luck with the hunt.

Thanks for your kind words of encouragement. I have decided to specialise in machine learning. It perfectly suits my analytical and technical appetite. Also I would love to work in robotics so it seems like a natural path. Btw: nice site http://codingforinterviews.com/ . I will definitely give it a go :)

Don't work in a company with the people who told you that. It's not only wrong, it's bad for business, and I constantly see the negative consequences of this worldview.