Ask HN: How does an old timer find contract work

81 points by zanethomas 2 years ago | 46 comments
I'm 72 years old and have been programming professionally since I was 27. I’ve kept up with the times reasonably well, considering that no one can now keep up with more than a few branches of software’s evolution. Sparing you the history: over the past 8 years I’ve worked extensively with javascript, full stack, taught full stack at a bootcamp for a year, written a couple very large applications, and worked a bit on other projects.

I would like to find more opportunities to continue doing what I love the most. At this stage contract work ranging from ~20 hours per week up to > 40 hours per week occasionally is probably the best value.

Yes, there is a question.

How should I go about finding such jobs?

(Also, I’m unclear about how to briefly fit my 45 years experience into a resume format)

  • gregjor 2 years ago
    Freelancer at 62 here, 40+ years programming and system admin experience. My opinions/advice:

    Word of mouth and professional connections work best. With your long career you must know a lot of people who run companies, or still work in the field. And they know people. Word of mouth and referrals remain the best way to get leads.

    Freelancers should focus on solving problems. Employees get hired to fill roles. Freelancers don't need a resume. They need demonstrated expertise that they can apply immediately to solving business problems. My approach comes down to getting the (potential) customer to list and describe their top five or ten pain points or needs, in priority order, then knocking those out for them. If you can deliver no one cares about your age or what you did before or where you went to school 50 years ago. Working remotely also helps, because you won't get the "not a good fit with our culture" excuse (i.e. "too old").

    If you mean contracting like a temp employee that usually works more like an employee arrangement -- resume, interviews, etc.

    You can work through an agency (disclaimer: 10X Management represents me). A good agency does the marketing, contracts, legal, invoicing, payment for you (for a cut). They can expose you to opportunities you would not otherwise know about.

    Focus on your strongest skills, don't try to do everything. For example I concentrate on relational databases/SQL (core ideas and techniques almost unchanged since the 1980s), Linux system admin and cloud infrastructure (old hat to anyone who grew up with Unix), and web application development. I started freelancing by finding customers who had abandoned or broken projects (plenty of those, like 60% - 90% of all software projects) and offering to fix the problems. Debugging and maintenance pay just as well or more as green-fields development.

    I have several articles about freelancing on my web site typicalprogrammer.com. No ads, sign-ups, pop-ups, or affiliate links. Good luck.

    • mr_o47 2 years ago
      Glad it worked out for you. After reading this I’m motivated to start out as a freelance and can you talk to us more about how you turned this into a fulltime career

      From most people I have heard is that they usually freelance as part time

      • gregjor 2 years ago
        That's funny, all of the freelancers I know do it full-time.

        I started freelancing part-time when my full-time employer started losing money and laying people off. I had a friend who ran a web design company, he would hear from his customers how they needed web programming, so he sent that work to me. He introduced me to another design firm that had even more clients who needed help. From there it kind of snowballed. By the time I quit my f/t job I had replaced my income with freelance work.

        You don't have to freelance full-time, 40 hrs/week. You need to work enough at a good rate to get the income you want. If you were making $100k at a full-time job that's about $50/hr. If you can get $100/hr freelancing you can either work 40 hrs/week and make $200k, or work 20 hrs/week and make $100k.

        My advice: Get some customers first. Concentrate on establishing long-term relationships. That will mean doing some not-so-fun work and maybe expanding your range, learning the business domain, doing a little extra for the customer. Try to keep non-billable time to a minimum. Don't spend a lot of time/money on stuff like incorporating, fancy web site, business cards, complicated banking, accounting, lawyers. The biggest non-billable time suck for a lot of freelancers is finding and bidding on jobs. The less churn you have with your customers the less of that gig-hunting you have to do. You want to build a good base of steady customers who will refer you to other customers. Ideally you get your customers on monthly retainers, which turns you into a predictable fixed monthly cost instead of an unpredictable account payable.

        Remember that as a self-employed freelancer you have to pay all of your Social Security, Medicare, and health insurance, so factor that in when determining your rate.

        In the freelancing articles on my web site (typicalprogrammer.com) I suggest charging for specific tasks and deliverables, not big vague fixed-fee projects, not hourly. That doesn't always work, it depends on the customer and the task. You should have a target rate in mind, of course. If you want to make $100/hr and your customer needs a task done you estimate how long you think it will take and multiply by your rate to get a fixed fee for that deliverable. Then stick to that. Estimating large software projects challenges even the most experienced programmers and managers, but with some experience you should be able to estimate well-defined tasks that take less than around 40 hours. That also keeps you from getting in the position of your customer owing you a lot of money, or you owing them a lot (because you took a 50% deposit up front on a $20k project and you can't deliver, or you client refuses to pay the remainder). I vary my exposure based on my experience and trust with the customer, but for a new customer I would not want to get more than $2,000 to $4,000 in the hole, so I will break their tasks down into small measurable deliverables I can bill for.

        • cweagans 2 years ago
          > You need to work enough at a good rate to get the income you want. If you were making $100k at a full-time job that's about $50/hr.

          This is further clarified in the rest of the comment, but I wanted to call attention to this. Be really careful with this line of thinking. It's not an apples-to-apples comparison, especially given higher costs and potential downtime between contracts. I recommend billing about 30% more than you'd expect out of a salaried position.

          > I suggest charging for specific tasks and deliverables, not big vague fixed-fee projects, not hourly.

          Why do you recommend this? For beginner freelancers, time and materials is an excellent way to go. For fixed bid (on any scale), if you overestimate something and get it done quicker, you get a nice bonus. However, if you underestimate something on a fixed bid, you're now eating the difference. In my experience, software projects tend to trend higher than estimated way more often than lower. This seems like a recipe for an unexperienced freelancer to get screwed by their first engagement.

    • iancmceachern 2 years ago
      The best method I've found for contractors to find work is to mine linkedin.

      Although it's against the linkedin terms of service (and I do not currently use it), octopus crm is a good place to look for thr framework, octopus automates it, but you can just do what octopus does, follow the same playback, manually.

      Every day like a few people's posts, write a glowing reference/reccomendation for someone you've worked with or for on their page, endorse a few people for skills, and send out 10 personal messages to people in your field. To find those people search . Like if your into semiconductor robotics just search for that with those keywords, then filter it by people in management, then further by anything else you want to filter by (location, etc) and then connect with those people (send a friend request) and in the note just say hi, I'm X, I do X, I noticed you do to, just wanted to connect.

      Do that for a few weeks and someone will reply back asking for your help.

      I hope this helps, if it doesn't ignore it and do something better.

      • gregjor 2 years ago
        I signed up for LinkedIn when it started, stayed on until last year because I believed it offered some value to me. I never got a single lead from that site. I would call it useless unless you need to fill a recruiter's candidate database, or if you have the patience to spend a lot of time building a fake network of people who don't know you through "likes" and posts. Your mileage may vary. I ditched LinkedIn along with all other social media except HN and that has not affected my freelancing prospects at all.
        • HeyLaughingBoy 2 years ago
          YMMV. I got my current position after a recruiter saw my LinkedIn profile (that was about 5 years old!) and contacted me last summer. I wasn't looking at the time, but it didn't take much to convince me to leave :-)

          [edit] That said, for a freelancer, LinkedIn has less value unless you are active in the same communities that your customers are.

          • gregjor 2 years ago
            If I was looking for a f/t job I might use LinkedIn, mainly because so many recruiters use it. In my own career, both with f/t jobs and freelancing, referrals and word-of-mouth always work best. A good recruiter can put you in front of hiring managers, but I would prefer finding a good recruiter face-to-face rather than on LinkedIn.

            I think the worst way to find a job is filling out applications online and blindly sending in hundreds of resumes. LinkedIn at least sits a notch or two above that.

          • satvikpendem 2 years ago
            All my jobs have been from recruiters on LinkedIn. I keep it open and get at least 10 messages a day talking about this or that position. I guess people don't optimize their profile like LinkedIn tells you to, after you do that, it's very easy to get inbound leads.
            • gregjor 2 years ago
              Are you getting freelance work on LinkedIn, or job leads from recruiters? When I had a LinkedIn profile I got lots of contact from recruiters (both internal and external). Since I'm not looking for f/t jobs I just replied "Thanks but not interested."

              I'm sure LinkedIn has value for some people, probably even some freelancers. It never did for me, I always found referrals and word-of-mouth work better.

            • iancmceachern 2 years ago
              You were clearly doing it wrong. I've done the opposite. I've built a robust network of real people that have real mutual interest in being acquainted with me professionally. You have to put good will into it. It's not a site, it's not linkedin, it's a tool to meet cool people who share your professional interests and to facilitate making real connections with them. If you used it to create fake friends and superficial relationships that's on you.
              • gregjor 2 years ago
                Not sure how you got the idea I created "fake friends and superficial relationships," I think you misread my comment. I intended to dismiss that plan because it seems the norm on LinkedIn -- "connecting" with people you don't know, haven't worked with, for the sole purpose of creating a fake network. My LinkedIn network consisted entirely of former colleagues, customers, and a couple of recruiters I have worked with. Turns out I can stay in contact with them in person, by phone, or with email.

                Maybe it comes from my age, but "connecting" or "liking" someone on social media doesn't equal "meeting" people, cool or otherwise. A referral is a referral, perhaps, but I think one from someone I worked with or for who can vouch for me counts for a lot more than one from someone I "connected with" on LinkedIn.

                My personal address book keeps my "network" safe from anyone harvesting them from my LinkedIn profile, another bonus.

              • iancmceachern 2 years ago
                What is your advice for OP in how to find those prospects? This is a thread with that goal in mind, do you have any advice for him on how to find prospective clients?
                • gregjor 2 years ago
                  Yes I answered in other comments in this thread. I have a couple of long articles about finding freelance work, how to work with freelancers, and maintenance programming as a career on my web site typicalprogrammer.com, which I mentioned in my reply to OP.
            • brynb 2 years ago
              Any old timers here in the thread, please email me at strep_makers.0p@icloud.com — I’m building a new company doing both consulting and internal product development and have always loved working with older, more experienced folks. We’re looking for tech leads, technical project managers, and anyone who has the ability to take strong ownership.

              (FYI, that’s a burner email— I’ll reply from a different one)

              • kleer001 2 years ago
                > I would like to find more opportunities to continue doing what I love the most.

                Lean on face to face networking? Programming Conventions? I got my last couple jobs based on who I know, not from applying in a big 'o cattle call.

                > briefly fit my 45 years experience into a resume format

                Chop it to just the last 10 years? That's what I did (as a green 45 yo with 20+ years experience). Then, during the interview I talked a bit more about my full experience.

                Best of luck!

                • gregjor 2 years ago
                  I have never formally interviewed for freelancer roles. I don't interview car mechanics or plumbers -- I pay them to fix a problem and expect (sometimes wrongly) that they know their business. When I get a freelancing lead the customer doesn't usually care about my experience, education, age. They want to know if I can fix their business problems. Either I can or I can't. If the customer does try to start an interview with me I change the subject to focus on what problems they need to solve. My job as a freelancer/consultant amounts to quickly understanding the problems, setting priorities, and fixing things. I'm not auditioning for a f/t job.
                • _tom_ 2 years ago
                  Write and speak.

                  Have an online presence in some area. Open source something related to what you want to work on.

                  Help them find you.

                  • NtochkaNzvanova 2 years ago
                    Others have already hit the major points about finding opportunities (networking, word of mouth basically).

                    As far compressing your resume, my suggestion would be to pick and choose the few past experiences / accomplishments that you are most proud of or are most relevant to the kind of opportunities you're seeking. In other words, what would you actually want an interviewer to ask you about. Don't include dates. This approach is better than trying to write a detailed accounting of your entire career, even condensing each role down to a single bullet point. I'm coming from the perspective of someone who has screened resumes of and interviewed more experienced candidates in the past. It is definitely a bit of a turnoff when you receive an 18 page resume containing an essay about every project the candidate has ever worked on.

                    Same for listing keywords / technologies you've worked with -- no need to list every language you've worked with since 1975 (unless you're looking for roles as a COBOL or PL/I maintenance programmer). Focus on relevance.

                    • dv35z 2 years ago
                      You ought to check out UpWork (https://www.upwork.com/) and Fiverr (https://www.fiverr.com/). Treat it as a "buffet" of interesting work, projects, and skills. Likewise, you can hire other workers to help you with tasks, and then form your own virtual team. For example, If you'd like to build a mobile app, you could use those apps to find a graphic designer (someone skilled at Figma, in order to do design & prototyping), a back-end engineer (in order to build APIs), and a product manager (manage requirements, backlog, development cadence), and a skilled mobile app developer to build it. Depending on where your interest and skill level is, you can always pair-collaborate with these people - you'll learn a ton, feel the team vibe, and feel less "behind the times", since you have now augmented yourself with experts. Most importantly, treat the team well, prioritize quality, and have fun.
                      • khaki54 2 years ago
                        This is fine advice. I kind of like upwork because I can find someone, give them a small task, see if I like them and how good they are to work with. Then I basically fill up their pipe as things go well. After a few jobs you can usually work off of the platform so they make better margin.
                      • quickthrower2 2 years ago
                        There is freelance thread on HN. You could also apply to regular jobs, but make a note you are looking to work as a freelancer. Smaller companies, where engineers are the first screeners not HR/recruiter might receptive. A "burstable" resource who does 20h but might do 40h occasionally when needed might be an attractive concept to many companies.
                        • PainfullyNormal 2 years ago
                          Does anybody find work on that thread anymore? And by "anymore" I mean in the past year. Postings and activity seems to have dropped off.
                        • ushercakes 2 years ago
                          It's hard starting out.

                          Let's look at the opposite end of the spectrum. People that have more requests for work than they have time. This is common, especially in your field (programming).

                          So - a hack I like to suggest. Befriend one of these people! They exist on reddit, twitter, etc. Find them, they love humble bragging "ah I turn down jobs all the time nbd".

                          These people are like magnets for jobs, and because of that, they are also extremely credible sources of referrals. Hey xyz! I heard you are turning down a lot of jobs because you're too busy. Do you mind sending those my way?

                          Hope that helps.

                          • justsomehnguy 2 years ago
                            > Also, I’m unclear about how to briefly fit my 45 years experience into a resume format

                            You don't. I have a way less experience and I still only show my last 10 years. As I said somewhere, if someone is interested in my experience in managing a (now) 15 years old specific software then I is not interested in them.

                            Also I'm in favour of 'CV should fit on a single page'. If someone looks for talent then this is more than enough to interest them and nobody looks at the second page anyway.

                            • ilaksh 2 years ago
                              I think it's similar to what works for a lot of people regardless of age. Focus on a particular niche, learn how it works to the degree that you would be able to participate in that business, build tooling that would help you do that, let the people in that community know. The people who use you tools will ask you to make more tools.

                              To avoid ageism, focus on online communities on Twitter and Discord. They don't even need to see your face. 99% of the time they are happy to do a text or voice chat.

                              • HeyLaughingBoy 2 years ago
                                Create a LinkedIn account and contact recruiters. Many of them specialize in placing contract jobs. I also notice that they have been getting really aggressive these days.
                                • mylons 2 years ago
                                  i'm currently running https://hourly.fyi and aggregating some jobs here: https://hourly.fyi/jobs
                                  • brudgers 2 years ago
                                    Talk to all the people you worked beside, below and above.

                                    If they won’t turn you on to work, there’s probably a reasonable reason.

                                    Working with peeps who know you and your work doesn’t require a resume.

                                    And the first step for finding work is always seeking rejection - because that’s the typical outcome of a phone call - on the phone not writing a resume.

                                    A resume is only needed when someone asks for one.

                                    Good luck.

                                    • atlasunshrugged 2 years ago
                                      I don't see a downside from signing up for sites catering to folks with lots of experience. I'm biased, but Tribe.ai is great if you're interested in AI/Data related projects, but there are other platforms from Braintrust to Toptal which will help match you with projects.
                                      • goddamnyouryan 2 years ago
                                        This is one of the several problems we’re trying to solve at https://polyfill.work
                                        • zanethomas 2 years ago
                                          I'd like to thank everyone for the input received thus far and the future feeback to be received. It is very much appreciated and will be given very careful consideration!
                                          • stocknoob 2 years ago
                                            I might try approaching companies & services that target senior citizens. Having a developer who understands the target audience is a huge bonus.
                                            • giantg2 2 years ago
                                              Wow, I'm in my 30s and feel I'm too old to keep up already. Good for you.
                                              • readonthegoapp 2 years ago
                                                what's your email? you can put it in your profile. i'll ping you about a potential part-time contract. thanks. psmithsf@gmail.com
                                                • akhmatova 2 years ago
                                                  Know that the odds are stacked against you - but be persistent and press on anyway.

                                                  The minority who are willing to look past your age (who will also be the better ones to work for) will pick up on your persistence and see it as a positive trait and hire signal.

                                                  As to the resume - there's lots of advice out there on resume advice for older workers. Truncating / condensing lists of older gigs is one of the standard techniques.

                                                  The rest of what you do is a variation of the same advice as applies to younger candidates - just that in your case it will have even more protective benefit,

                                                  For example - even though it may bore you a bit, be sure to both read (or carefully skim) as many modern books as you can that are relative to your field, as well as to stay up on the "shiny" stuff (cloud, containers, CI/CD) even though your gut instinct will (rightly) tell you they may be overhyped or less important than knowing the core principles.

                                                  That is - at least know what they are, what problems they attempt to solve and what they are basically made of. This will make is substantially less easy to dismiss you as a dinosaur (inflexible / crusty / less nimble than younger candidates).

                                                  Finally: wear your age with pride. You've lived through times, and have seen things these people can only read about (for those who even read these days). You have a rare perspective to offer, and the better folks out there will see that and dig that aspect of you. And will be proud to have you in their corner and on their team.

                                                  • gregjor 2 years ago
                                                    The "shiny stuff" is almost all retreads and new clothes on old ideas. Containers and VMs? Around for decades in various forms. Cloud? That was mainframe computing years ago. CI/CD? Had it back in the '70s. Same with TDD. A hallmark of the software industry: almost nothing truly new gets introduced, but old ideas and technologies get a new coat of paint, a buzzword, and make more sense today because the hardware and networking have improved by orders of magnitude.

                                                    Anyone who learned C back in the '70s or '80s can pick up most newer languages quickly. Relational databases, the core of every non-trivial business application, date from the '80s.

                                                    My advice: don't worry about or focus on your age, don't make excuses, don't try to persuade people you haven't turned into a dinosaur. Focus on business needs and how you can solve problems and add value. Ageism in tech certainly exists but you mainly run into it when a team of younger people interview someone their dad's age and don't see a good fit with the team. And they're right about that -- I won't work 18 hrs/day for free pizza and beer anymore, and I don't play foosball or need a nap room.