Ask HN: Going from 12 years of self-employment to tech job? | Hacker News Reader

Ask HN: Going from 12 years of self-employment to tech job?

39 pointssenordevnyc39 comments

I've been a self-employed consultant for 12 years, worked on dozens of native iOS apps, including for some name brand companies, I've made $300k-400k gross for years, and I've also started my own profitable side business (hundreds of thousands in revenue over the last few years).

Being self-employed has been amazing, but I'm looking for a new challenge and to level up even more over the next 10-15 years, so I'm going to be applying to the Big N companies with offices in NYC, as well as some tier 2 companies. I'm looking for senior roles, maybe even staff? I don't know if that's realistic though. I've been grinding on my data structures / algorithms and I'm feeling good there.

I've shared my resume below, welcome any constructive feedback, no matter how brutal. Am I delusional to think I have a shot here?

Resume: https://imgur.com/rFXKHPk

View on HN

I did the same.

I found that big companies (the Tier 2 telcos, etc) either couldn't afford me, worried about scalability/teamwork skill, or just didn't like what was on my resume. They want people who fit in well as a cog into their corporate machine. There was one pleasant exception to this, a small team carrying a billion dollar company, but I felt the company had too many processes and moved too slowly.

The startup tier jumped at the opportunity though. I got my current job offer in less than 24 hours after the interview, even though I requested a salary on the high end.

There's a lot of pros to jobs. I was used to working about 4x the average speed to justify a 4x hourly rate, and now I can work half as hard for double the median salary. It also means that time isn't money anymore, so I can take off more time to read books or just go shopping with my wife.

As odd as it sounds, I have more free time than back when I was working 10 hrs/week from home. It's nice to not have to worry about marketing and collecting payments.

Oh one thing to add is that a lot of them didn't like seeing a list of projects. You should list maybe 3 or so.

If you can make a living freelancing, they know you can code. They're looking for how much impact you've had on the project, or whether you work well as a team. As well as what kind of long term benefits you bring - can you branch off a subsidiary on your own or expand a product into other markets?

Thanks for all the feedback, really appreciate it. I think you've nailed the pros / cons. I've really enjoyed self-employment, but I'm honestly a little bored and burnt out. Ready for a bit of a break.

> I'm going to be applying to the Big N companies...

Don't apply to companies. HR Flunkies & Recruiter Bozos won't apprecaiate your background.

Instead, reach out directly to the guy you most help. Think CIO/CTO, Heads of Engineering. Linkedin is good for identifying these people.

You have a shot, but why? Dealing with the politics of corporate is bad. Don't care which of the FANMAG you work for. Let alone for smaller companies. You'll be wanting out very fast.

I don't know that your resume will even get you a call back. There's nothing that jumps out. Things like C/C++, Python, Go, Distributed Systems, etc. The first thing you need is to get seen, then pass the phone screen, then get onsite. For an IC, if you can whiteboard it then you might have a chance.

Best of luck tho.

I hear the cynicism, I do. You might be right, but I have friends in these companies and some love it, some hate it. I want to give it a try.

As for the resume, maybe we've miscommunicated? I'm specifically looking for an iOS role, so having Python and distributed systems on my resume doesn't seem like it would help me?

I do appreciate you taking the time to post though!

Your timeline and mine align somewhat. I got out of military by 2007 and started up working for the fruit company in 2008/2009 then went outside to but stayed within the iOS ecosystem from 2011 to 2013 and did indie work from 2014 onwards. I'm opting for product roles instead of engineering roles as it's a better story fit for explaining how to use my product leadership skills and leaving the dev part to the younger and cheaper leetcoders they want to groom.

Life is really different on the inside tho. You move way, way slower and spend more time dealing with people than with code.

You've been making 300K+ for years as a consultant, for more than a decade? Yes, you have a very good shot, because you have a demonstrated track record of being able to do the work.

I don't know if you have a shot at a job that pays 300K+, though. I don't know the NYC market.

I’m in a similar boat as OP, and I can tell you that folks are VERY skeptical of success when you haven’t been a part of the corporate rat race. My success has a consultant has (so far) apparently little relevance to passing interviews at FAANG and the like. People like talking to me though, so I guess there’s that!

Ugh, don't love hearing that! However, it does sound like you're getting interviews? Are you saying your work hasn't prepared you to pass those interviews? If so, I definitely agree, which is part of why I took a data structures + algos class and why I've been brushing up on whiteboard interview skills.

Companies want loyalty. Beeing good at what you do has almost no importance above a very basic level. Loyalty is important because they have all kind of internal crap that is not documented, not organized and which you will accumulate if you stay with them 10+ years.

Also, beeing a consultant shows that you are independent, but what they want is conformism, people with no ideas of their own and so, not independent. 99% of companies fit this profile.

What you say is true, however, I think it's less about loyalty and more about risk mitigation. Companies don't want to take chances that the super-star programmer they just hired is a renegade cowboy. I get that. But no about of LeetCode prep will dissolve that preconception.

Companies want leetcode, not loyalty

While companies want loyalty and will incentivize loyalty, what's to say a former consultant isn't loyal? Consultants take huge pay cuts to work under a boss. They're more resilient to competing offers and won't jump for a 10% offer. They're often sick of being their own boss and are less likely to quit and do a startup. They're used to taking on massive stress, and sometimes even being the scapegoat for it

So in some sense, ex consultants are better loyalty per skill level compared to many lifetime FTEs.

That's a nice insight but lets see who are the bosses that do the hiring in large companies? They are people that stayed in the same company for 10-15 years. What you wrote looks strange and even silly to them. Otherwise they would have become consultants themselves long time ago. Even if they aknowledge that you are indeed very good, their little ego will not let them hire you.

To answer more directly to your comment, it doesn't matter that you are actually loyal if their perception is that you might not be. In fact they just don't know what to make of you. They never met somebody like you.

Yeah, that is probably true. Big companies tend to hire entire companies to outsource work to, even when those companies are less efficient than individuals.

I did notice that all the corporate people have nearly zero mutual friends on Facebook, whereas with consultants and startup people there might have well over 100 mutual friends. It's quite an extreme.

Agree on this very much

Apologies for being off topic, but I'm looking to attempt the opposite transition. Go from Big Co to self-employed consultant and would love to pique your brain about your journey if you'd be willing to field a few questions of mine at some point?

Unless you plan to excite the OP with your questions, I think you want to pick OP's brain.

Haha the most exciting questions OP will ever hear!

Hi, I work as a recruiter and your CV is strong enough for me to be able to submit you to one of my clients, a publicly-traded online gaming company with tech HQ in Jersey City (few minutes from Wall St via the PATH train). They're really into functional programming but I have you in mind for the Senior iOS role.

These hints should be enough for you to reverse-engineer the company name, but just email me and I can share full details as well as submit you into the interview process if you're interested.

Appreciated, dropped you an email.

The last few months I have gone back to studying, and have undertaken COMPTIA A+, COMPTIA NETWORK+, COMPTIA CLOUD+ and COMPTIA CYBER SECURITY ANALYSTS. All due to the lack of suitably qualified cyber security analysts in Australia. If you guys have any advice I am all ears....I have a couple more months to go before I pass the exams...

I have no idea if you have a shot, but a good way to test the grounds could be doing the Triplebyte process. It's all online, you have those standardized technical test that big companies use and you get good feedback from those.

Thanks for the suggestion! I'm planning on doing TripleByte, Hired, and possibly some more mock interviews with Interviewing.io in the next couple weeks. I think my main concern is whether I can even get to the phone screen step with companies that don't work with something like TripleByte. Will they glance at my resume and think I'm not remotely qualified because I've never had a "real" software engineering job?

Work with a good recruiter? The incentive will be aligned in preparing your resume to be accepted by the big companies

Hey, founder of interviewing.io here. We're not just for practice. If you do well in your mock interviews, you can book interviews with companies like Microsoft, Twitter, Coinbase, and a bunch of others with 2 clicks. Literally no one sees your resume, and you get guaranteed interviews at companies.

I can't promise you we have all the companies you want, but unlike Triplebyte, you can choose which companies you want to talk to, and you don't have to talk to anyone, just book.

Sounds pretty good :)

Curious: any issues with using more than one of these kinds of platforms, or do you guys have exclusivity arrangements? How does it work if I've already applied for a role at a company that I then connect with on your platform?

No exclusivity! You should do whatever you can to maximize your chances.

If you've already applied at a company and were rejected based on your resume (ie you never talked to a human), you're free to reapply through us. One of the most recent hires we made at a top tier big co was rejected 3 times based on resume before he got in through us!

off topic but can you share your rise to 300-400k/year? Do you just bill more than your previous contract? i.e. 125/hr last 6 months, so at renewal time you jump to 150-175/hr? Did you work 2 or more jobs at the same time? It seems like 300-400K/yr remote work in a low COL would be the dream setup for most of HN, but to each his own. What's the take home on your salary after expenses/taxes?

Likely billable rate of $100-$150 at 2000 hrs per yr. Earlier on during the iOS dev crunch of 2010-2012 billable rates were hitting the $200+ mark. From 2013-2016 those rates dropped down to $150, in the past 4 years those rates plummetted to $80 and now lately even $40. Unless you're working on extending some native API or have expertise in the newer ARKits and HealthKits or you're adding value elsewhere in terms of PM or design or marketing it's harder to justify the magical $100 rate.

I never ever bill hourly. 90% of the work I do is value-based pricing, with a weekly or monthly rate once in a blue moon. My effective hourly rates are much, much higher than anyone would pay me strict hourly.

Also, I'm not sure where you're finding clients, but the market for senior iOS dev definitely is nowhere near $40 / hr. If you're competing with offshore devs on Upwork or people who do "web, iOS, Android, and anything else development!!" then yeah, maybe. But there are tons of clients out there who need senior talent with deep iOS expertise and professionalism and pay north of $100 / hr, or much more if you price based on value.

Would you mind giving an example of the type of value based pricing you're talking about? What kind of metrics do you use to determine the value you provide to the client? Is it as simple as "this feature has increased sales by X%"?

I would go to https://www.nycjobsboard.com and apply related position.

How are you going to deal with the psychological impact of the transition from your own boss to working for someone, on-site, following full office hours?

That's actually kind of the goal :)

I've almost never worked from home, I've always worked out of my own office, shared an office with another freelancer, or worked from coworking space. And I've also always kept a pretty typical ~9 to ~6 schedule Mon-Fri. So I'm not sure those things will be a huge adjustment?

In that case all you have to watch out for is office politics ;)

Hmm your background as described sounds good but your resume is not well written. Learn about resume writing and start from scratch. I’m sure you must have a better pitch for your clients if you’re pulling those rates. And I also question why you’d join a bigco if you’re making those rates while running a successful side business.

Reply on news.ycombinator.com