Ask HN: Been self-employed for 18 years, am I hirable?

My resume looks like this post: all over the place. It almost seems like it's all amateur work, because so much of the "cool stuff" was done for internal consumption in my own business or for clients, and I've (effectively) had one employer for 18+ years. The stuff that is publicly available is quite political in nature. But none of it is amateur work; I'm a damn professional, and I know what I'm doing…but I'm not so stuck in my ways that I'm afraid to ask for help when I need it.

Starting, running and succeeding in a business shows beyond a doubt you have skills to at least deliver a business result.

For _every_ point on your resume ask yourself if it is useful from the companies prespective. Never put in just everything until you are applying as a just everything man. And even then they will take that guy who says: I am Fred, I am a Frontend Developer. Because they can imagine who Fred is and judge him by that.

Paint a very simple and tailored picture first, go more into depth later.

I am a “renaisance man” myself to the degree that some people won’t believe me when I tell them what I did. This is bad for job interviews and resumes. If you say: “I am Fred the Soundesingner” they will take you if they need a sounddesigner. If you say “I am Fred and I can do ...” and proceed to recite a endless list of things, they will be impressed, but they won’t know what is real, what made up and how you actually see yourself.

Apply as the guy who fits the position (if you like it) and not as the complex beast you really are. Never say anything that you can’t connect somehow to the company unless it is a hobby or so.

I have a couple of comments based upon my experiences of flitting between self-employed, contractor, consultant, employee over a couple of decades. Granted that my skill set is a small fraction of yours, yet I am seen to be rather eclectic as well.

Ageism -- I have to mention this up front. As the years go by, this has been an increasingly big hurdle for me. Employers want young, eager, keen, naive and cheap. Basically you are expected to work 70+hours for 40 hour salary.

Specialisation -- especially when contracting, the brief is for a specific domain and thus a small subset of your expertise. Having too much on your resume means that you are seen as a jack of all trades and a master of none. Managers' perceptions trump reality.

Consulting -- so much of consulting is (a) confirming the managements pre-ordained decisions; and (b) being the scapegoat when it inevitably all goes wrong. And even (c) to implement unpopular decisions for which they don't want suffer the push-back.

SME clients generally don't have the budget for getting the job done properly.

Ok, enough of my cynical negativity.

I think that you need to focus and tighten up your strategy. Perhaps clearly identify the exact type of companies you want to do work for and then determine where you can render the greatest value. Having done that, then you would pare down your resume to focus on the exact results and technologies that are applicable and leave off the rest.

Having an existing B2B client base, I would be tempted to review other areas where you could deliver results for those clients. Yes, it is hard to break out of the pigeon hole that you have been consigned to, but at least those clients know that you deliver great work at competitive rates. Generally it is easier to win over people you know than when you are cold calling.

No one needs to know who owns the Co, as long as you can support what resume says.

Anyway if you really do know what you're doing (heh heh), developer evangelist sounds like a good idea, or some kind of architect or team lead type deal (though of course management is its own skill set). You already convinced me you've got a lot on the ball, via your blurb here, so I think yes you'll be fine and you're hirable. Though if I were doing the hiring, I would want to suss out your "close collaboration" chops, since that would be the one thing not explicitly demonstrated by one's history as a solo consultant. Maybe I'd make you do some pair-programming and see what happened!

Yes, if you ask people you worked with and respect your technical skills.

How do I craft a resume?

Don't expect to be successful sending resumes to people who don't know you. You are too far out the norm. Use your reputation to get warm introductions.

You're going to get inquiries about agile, test driven development, release cycles, code reviews, build pipelines, and overall dev team processes that you're familiar with.

Like other comments here, focus your value as a senior dev, maybe even on certain stack or framework.

Good luck to you sir!

It is incredibly hard to find contracts and jobs. "Normal" resumes let you slot into something at this time in your career where everybody knows what they are getting. With you, it's a risk -- at your best you will be brilliant and double their revenue, at your worst you could destroy the company in a year. Nobody wants to take on that kind of risk, even though it might be the best hiring decision they ever make, so your resume will be passed over. Every single time.

It's not that you don't want to fit in to corporate life: you probably genuinely want to get a job right now so that you can have some assurance of income and stability in case you get sick, asset protection, etc. etc. It's just that, well... I predict that you just simply won't be able to, no matter how hard you try; no matter how important it is to you to keep a job or a contract. You won't even recognise what it is that you are doing that causes friction and problems. It's another universe, and you haven't lived in that universe enough to absorb its norms and culture. You are an alien.

What I did after failing on the "get a job" route: I put together enough "product stuff" quickly that I was able to get a buy-out and then act in a senior role in the buying company for a while. A year in a corporate role, and you'll remember why you never wanted that life 18 years ago. So, no, this route doesn't work either and I don't really have any answers to your problem yet. Sorry.

Gig platforms might work for you, because then nobody needs to know how old you are or what else you can do.

Are you sure you can't scale or grow your consulting/development/training business? Just have a coffee with every single customer you've ever dealt with that remembers you and see what happens. It will be easier than trying to get a job or a long-term contract.

Feel free to message me to talk further.

They're pretty much all VP-level or above, and have titles related to Digital (Strategy|Innovation|Transformation). They primarily serve two roles:

1) Public speaking/Networking. A huge component of their role involves speaking engagements and demonstrating competency/thought leadership. Which interplays both their personal branding and splashes back on our agency's branding.

2) Thought leadership with clients, usually marketing teams, that want to integrate stuff like chatbots into their marketing efforts, machine learning, improving website experiences, etc. For traditional companies that don't sell direct to consumers, a lot of stuff that seems trivially easy to measure and optimize becomes incredibly difficult, because you're measuring through proxy metrics and indirect aggregate figures from retailers and fairly complex multi-party logistics.

These people rarely do much actual coding, but they'll essentially be the visionary/solutions architect for these projects, and own them from client pitch through to post-engagement follow up. As well as use them as case studies to pitch similar work to new clients.

Your experience running your own consultancy as well as your public speaking chops would be a significant advantage for these types of roles. And your active technical competency would be perfect for the subset of engagements which have aggressive and potentially antagonistic IT teams that you need to get on the good side of.

Pretty much every large marketing agency has these types of roles, but you generally only work your way into them via networking. It's a potential area to look at, though.

Get clarity around your target.

Look for the individual YOU best can help. Likely a Founder, CTO, or VP Engineering of a growing company.

You'll find them at Meet-Ups, Conferences, and Trade Shows.

https://www.moonlightwork.com

Why not curate the things that you've done on a portfolio page which you can use to evidence the extent of your competency? You're in a rare position to have produced a lot that you can show, so I'd suggest maximising it.

Another poster suggested having a coffee with every client you've ever had and seeing what happens. Definitely do this. If you have 20 years worth of clients there should be a lot of power in your network; especially if your clients think highly of you.

For concrete steps, write down what you want (expand on what you put here about making a difference). Remote? In a certain city? With what technologies? Managing people? Etc. Try to narrow it down.

Then I'd recommend building a spreadsheet. Go into your LinkedIn and look at first and second level connections. Make a note of anyone who works at a company that looks interesting.

Looking at each company's careers page might be helpful, but they aren't always up to date. Definitely don't submit a resume via the page!

Then I'd reach out to your contact and ask for a quick meeting to learn about the company (if first tier) or ask your connection for an intro (if second tier). Learn about the company needs. Ask some smart questions. If the company continues to be interesting during the call/email thread, ask about positions. Crucially, I'd ask the contact if they know anyone who is looking for someone like you. This level of indirection both opens up your options (because they may know someone else that you haven't thought of) and spares the contact of the awkward "uh, we aren't hiring" answer that you might get of you asked directly "do you have a job for me?" (which, no matter how you couch it, puts them on the spot).

And make sure you follow up if given any prospects. Even if you just close the loop with someone who gave you a contact and say "hey, thanks for the intro to person A, I chatted with them briefly and it wasn't a fit."

Also note that this doesn't happen super quickly so I'd keep up with your current business until you have a signed offer. I have found that companies are ok with flexible start dates or my contracting back during a transition period.

But yes I think you are hireable.