
Ask HN: Been self-employed for 18 years, am I hirable? - hirable_taway
Throwaway account here, but been on HN for a long time. I&#x27;m going through a big life change, and this post is going to ramble a bit. But I need your help, HN.<p>I&#x27;ve also been running my own business for a long time, mostly B2B consulting&#x2F;development&#x2F;training in the Microsoft&#x2F;Office world. But I don&#x27;t want to be pigeon-holed.<p>For my own company, however, I&#x27;ve done a lot. I&#x27;ve written many, many chatbots with various functionalities for many platforms (some incorporating NLP—spacy.io is a particular favorite of mine); developed many non-throwaway, high quality apps&#x2F;services with NodeJS, Python (Django), and Ruby (Rails); done video post-production and ingestion automation (latter via AWS, including Lambda); created many custom Wordpress plugins and themes; created more back-end mashups (NodeJS&#x2F;Python&#x2F;Ruby native, or via NodeRED&#x2F;Huginn&#x2F;Zapier) and built more web sites (I favor SSR—I guess because I&#x27;m an old?—but have a functional working knowledge of React and Vue) than I can count; I&#x27;ve &quot;done data science&quot; well enough to talk the talk (for text-processing and basic statistical domains); I&#x27;ve worked on &quot;citizen journalism&quot; projects that were well-received in, ahem, certain social media circles (my politics trend toward the more liberal end of the spectrum); I am an <i>EXCELLENT</i> public speaker (I&#x27;ve spoken at many conferences in my industry, and consistently get the highest rankings); and a lot more.<p>(…see my reply for more…)<p>I&#x27;d love to be doing something where I am making a difference, either with code, or maybe as a public-facing (speaking&#x2F;writing&#x2F;coding) developer evangelist.<p>I am the geek renaissance man of the 21st century, with the arthritis of a retiree, the dark humor of a comedian with their own Netflix show, and the ADHD-superpowers of a whole fleet of college grads.<p>Am I hirable as a contractor (or more)? How do I craft a resume that both honestly reflects this kind of history and does justice to the breadth of knowledge I have?
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atoav
My tip would be to gather really good intel on the company and the people they
are looking for and then...

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.

~~~
mettamage
Your answer is also a sentiment in other answers.

I just wanted to say: thank you for being so clear. I am starting my job
search but already have done quite a bit for a recent college grad and I'm
exactly hitting the issues that you're stating here.

One question: how can I make up for the fact that I did iOS development in
2014, web development in 2017/2018 and teaching in between (2015/2016)?

Should I just put a white lie on my resume and claim everything was: web
development, iOS development or education? Depending on the idea that people
who give references are willing to lie for me because they know what I'm
capable of?

It's a very directed question, I'm sure there are other strategies and I
wonder what strategy one should use for a gapped resume like mine (in terms of
web dev, ios dev or being a lecturer/teacher).

~~~
koolba
Lie as much or as little as you’d like. Employers assume that every resume
they get is padded with fluff. If you need to bullshit to get your foot in the
door have no qualms about it. All that matters is if you can walk the walk
once you’re in.

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rdiddly
I hate to be that asshole on the forum who, instead of answering the question,
asks "Why on earth would you want to do such a thing?" but in this case I am
literally that baffled, and that curious about what could be driving someone
to look for a "job" after all this time. You already seem to have everything
you need, and more than most jobs could offer. You said there's a big life
change going on, but if that were me, and especially if the change were
involuntary, I would try to keep as many things "the same" as possible to
minimize the number of things changing at the same time.

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!

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cosmie
I currently work at a marketing agency, and there's an entire team of people
that fit your background, although not usually nearly as heavily technical as
your history.

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.

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solresol
Your resume looks a lot like mine. Just replace the 18 by 19 and change a few
details and we could be twins.

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.

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valgor
"Hi. I'm really amazing and have done a lot of stuff. People love me. Am I
hirable?" /flex

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hirable_taway
I've been in the same industry (focused on a particular product line) for
nearly two decades on my own, but the work is drying up. I want to move on,
ideally doing remote contracting for a company that appreciates both the
wisdom and circumspection that comes with age, and the always-hungry/always-
learning attitude that comes with being a SMB owner for nearly 20 years. I
consider myself a hacker in the truest sense: I like to get my hands dirty,
and find the solutions that everyday consultants would miss, because I get my
hands dirty with everything, every day.

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.

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alain94040
_Am I hirable as a contractor?_

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.

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acutesoftware
Rather than say "Self Employed", you would put the business name you called
yourself under employment history and say you worked there for 18 years.

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

------
president
Depends on the kind of position/specialization/seniority you are trying to
break into but in general I've found that companies really only care about
algorithms in interviews. You can get almost any job in this industry despite
your educational background, employment history, soft-skills, emotional
intelligence as long as you are willing to hunker down for a few months and
review your data structures and algorithmic knowledge.

------
tinktank
Yes, absolutely. Reach out to recruiters for specific niches. I would value
you, staying in business for 18 years means you're doing something right.

------
CyberFonic
Wow! What an amazing breadth of experience and knowledge.

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.

------
mooreds
I was in something like the same boat, though my experience wasn't quite as
variable. I found that reaching out to the network was the most effective way
to get hired. You probably have a tremendous network of past clients and
people you've met over the years. Put that to work.

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.

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laurentl
Reading through your post, it struck me that your skill set is very close to
that of a CTO of a small startup (the missing part is around hiring and
managing, and maybe you’ve done that as well). At least it sounds a lot like
my first few months on the job: one day you’ll be setting up the company
website, the next doing some hacky back-end scripting, then some “good enough”
ML for a product prototype, and the next day you’ll be troubleshooting the
O365 corporate account. So this might be an avenue to look into... perhaps as
someone else mentioned by attending meetups where you’ll meet similar-minded
individuals who’ll be more interested in what you can do than what your CV
says.

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brett40324
Im sure you would do great in a full stack web application engineer role, or
lead, or other lead engineer role. I have to ask though, have you ever worked
on a team of developers, especially with one or many other teams with
engineers who have the same amount or more experience? If not, then that is an
area that may render some opportunities to be more out of reach,
unfortunately.

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!

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usgroup
I'm surprised that at the time of writing the word "portfolio" didn't seem to
feature at all on this page.

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.

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gesman
Put name of your company to your resume.

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

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nickwhite99
I’ve been in a similar situation and a question I always get asked... “what is
going to stop you from building something else in a year or so” (leading to me
quitting the job I’m applying for) best would be to address this issue head on

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JSeymourATL
> I'd love to be doing something where I am making a difference...

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.

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bjacobt
Moonlight work is good if you like to start with small/short term contract
gigs. I’m not affiliated to them.

[https://www.moonlightwork.com](https://www.moonlightwork.com)

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dmitripopov
Consider yourself a product you are a evangelist of and write your resume like
it's a promo. With all your experience it should work like a charm.

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KingFelix
Where are you located? Do you have some samples of stuff? I'm newish to HN,
can I send you a DM?

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gigatexal
Yeah I would think your years on business and dev skills would make you a
stellar hire anywhere.

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Cgjthrowaway
If you aren't hirable, then the rest of us are fucked.

