Hi fellows,
I've been pursuing my own projects for the past 5 years and dreaming about being an entrepreneur (aka the capitalist era Hercules) for the past 15.
I haven't succeeded, at least big time, yet. We also live in a very high cost of living location (mostly for the family/kid's sake if you wonder) so I can't really quit my job forever and continue my entrepreneurial journey full-time (I did a 1,5 year break previously and burnt through all savings though).
The question is, where do people like myself fit well in terms of full-time jobs and/or other ways of making money?
I am software engineer by training, but I've acquired business/marketing knowledge and skills over years, learnt accountability and people management, UI/UX and user interviews, bits of product thinking, analytics and decision making.
I feel like an entrepeneur, my skillset is very broad and, probably, quite shallow in some areas too. Perhaps it'd make a good CPO/CTO, in an early-stage company, but this comes with a tradeoff of being paid sometimes 2x less than a senior/staff at big tech and not much more than an engineer in a startup.
The reason I ask of course, is because while I'm experimenting, having fun and feeling good about myself, I feel like I am missing on lots of opportunities and probably being too risky about not buying a house while the clock is ticking.
Please share your experiences and thoughts, thanks!
I'm in a similar position. I think one of the challenges is that you can get a guaranteed high salary working full-time in tech. A great success in entrepreneurship might mean acquiring your previous salary after several years of working hard and making little money. Of course, you might also strike it right, but you might not.
I'm currently working part-time on retainer, which allows me to work less than full-time and still make enough money to live (definitely less than a full-time job, but enough to live comfortably). This leaves me time to build my own thing while not living off my savings.
I don't know what I'm doing, but I might suggest something like this. Stay at the job for now. Use the financial security to buy a house and get a good mortgage. Then start working on taking part-time work on top of your full-time job. This will suck at first (full time plus extra work), but once you feel comfortable about being able to get part-time work, you can feel comfortable leaving the full-time job.
> I'm currently working part-time on retainer, which allows me to work less than full-time and still make enough money to live (definitely less than a full-time job, but enough to live comfortably).
This is probably the way to go. Having _some_ income drastically improves the equation in your favor (due to tax laws and compounding growth).
Unfortunately, when I did this, I struggled balancing my time between the work as well as wondering if my startup failed b/c I half-assed it working part time or if its just not a viable business..
I can totally feel the 'half-assed' part. One of the real reasons I am avoiding getting a well-paid job is because it feels that it's impossible keep it and dedicate enough time to anything else really, let alone building a business on the side.
I'd caution you about giving up a well paid career.
In "The psychology of Money" the author warns the reader to don't make bets that need to go perfectly to plan. Creating a project every month until somethings sticks, requires that at least one of them can become a sustainable business. But if you can't achieve that, its very difficult to catch up to your peers or re-enter the workforce.
I spent the last 5 years working in Big Tech and have a large amount in savings where I plan on leaving, not b/c it make sense financially, but I just need something fresh in my life. Even if that fresh thing fails horribly, I have more than I need for retirement due to low lifestyle costs and careful saving.
There are a few "The Psychology of Money" books/talks including by Charlie Munger. Which one are you referring to may I ask?
Why not just work part time, seems a no brainer to me. Work 10 less hours a week, you'll keep up with your peers easily, and you'll have fresh time and projects on the side
8 years ago, the startup I worked at folded with an eng team size of 8. I spent 3 years working part time and side projects, my coworkers joined big tech (LinkedIn and Airbnb). They road the 2021 boom and ended up 1-2 levels higher than me with 3-5x more pay. 5 years after returning, I’m just now catching up to them.
TL;DR: part time basically pauses careers.
Thats unfortunate I'm sorry to hear. But it is also a sample size of 1.
My experience, working part time for 6 months, is that my side projects have differentiated me from other candidates, and get me a foot in the door for interviews. They usually say most candidates are the exact same, and the only way to differentiate and get an edge is: Perfect GPA; Successful projects; Sought after niche skills; Leadership experience.
But I've also had 2 relatively successful side projects (and tens of failed ones), so without those I'm not sure how I'd go
I’ve seen this advice before but I don’t personally know anyone who’s done it.
What makes it so hard to reenter the workforce?
I have a few friends that left tech for personal reasons and layoffs.
The ones that stayed out for a while, lost their ‘drive’ to reenter. They tasted the good life of no leetcode or on-call duties.
They make enough to support themselves but still less than half of what they could make in tech.
They realize their good life isn’t on the right trajectory and would like to reenter, but just don’t want to put in the effort, especially since the roles available to them are behind their friends that didn’t take a break
Take an "easier" but stable job. In this market, one needs stability over high income.
Spend your 30-40 hours at your job, drop to part time (3 x 10 hour days if you can) up-skill at your job, and use the extra 2 days to build stuff. Its very do-able
Thank you for your reply.
Re this: >I'm currently working part-time on retainer, which allows me to work less than full-time and still make enough money to live (definitely less than a full-time job, but enough to live comfortably)
That's quite a good position to be honest.
> Then start working on taking part-time work on top of your full-time job.
This is what I've been doing for the past 3 months but only to save some extra money as our main income is 90-100% spent on necessities every month. I charge per hour probably within the 50-70 percentile bracket in my location. But I can't see how I could charge more without being much more specific than just doing regular software engineering.
As a qualified engineer and owner (in terms of responsibility), I quite often get compliments on how well I handle things - with attention to detail, without oversight, pushing things to the completion, etc. This made me think that probably I'm lowballing myself with this (shitty) startup job.
But on the other hand, I don't know where else I could 'remain myself' in the way of not becoming a professional SLOC cruncher or, God forbid, the ultimate PSC-driven developer.
As someone whose transition to being more of a consultant, entrepreneurship is such a broad term that gets misinterpreted. There is no real job title called entrepreneur. What it sounds like you're really describing is that you want to capitalize on your skillset in order to generate additional income in which case it would be useful to think about what sort of activities do you actually want to do with your time? What fulfills you the most?
Here are some ideas that generate income but are quite different in terms of activities: - fractional CTO advisory services - engineering team coach - teaching at a local collage - writing a book
I'd stop worrying about your skills and start looking for opportunities. Start networking and finding people who have problems that can be solved with software and have a good market fit. Lots of people say "solve your own problems first" but software developers have a very unique set of problems that 99% of people and businesses don't have. Once you start to see how other non-devs work you'll start to see enormous inefficiencies and people crying out for solutions.
I joined an "experimental" team, basically working on low ROI strategic projects. A lot of them are from scratch, and there's a lot of ex-entrepreneurs who find it home.
B2B or unicorns usually have an experimental team because they have a major product that needs to be stable, and a team that isn't held back by all these processes. The NASA vs SpaceX combo, where one has to be really careful and make absolutely no mistakes, while the other tries to move fast and fix problems faster.
If you want to use a broader set of skills, try working in a developing country. Solve the kinds of problems that companies like Uber, Amazon, and Stripe can't. There's a lot of gap in existing infra and it's usually the unicorns that build it. Regulations are tighter because we have a lot of corruption to deal with - terrorists, business people, politicians, all the same risk category. They're also changing all the time because of this. Underdeveloped means documentation is constantly out of date and someone who can put together a hack while waiting for a partner to fix would be great.
How did you find this kind of team? I know you note B2B/unicorns can have these, but I have never found them myself. I find it difficult: Reach out to the CPO/CEO with something innovative or genuine passion for the industry area, and they either get you in excited and others in the C/tech suite are against you / already busy with projects, OR they see you as a threat and just talk to learn.
I am also wary because I have seen such teams before (e.g. a HTML5 team, yes silly as it sounds, web sockets and SVG felt like they opened entire new ways of making games), and a data science team using BERT etc (outdated totally by ChatGPT and made useless). Likewise I lead a team to adapt React (before it was predominant) which helped, and I was liked on the team by most for helping them code with less bugs (some of the old guard did not like using React). However, once that happened, it was done. My managers were changed, for someone who loved making lots of plans. I then got over-managed to the point I changed my career as it was obvious this manager had no interest in any future risks in the next 3-5 years of their time in that seat.
I just don't see stories where these teams somehow make a 2nd product for the company which actually successfully scales. They usually get eaten by being overtaken technically, or eaten by the main product. So what do you do after the "eaten" point? Does the company keep your around?
The textbook approach is:
1. Find product market fit
2. Get dominant market share
3. Work on the next cycle - the core business will go stale
4. Everything else in support - legal, finance, HR
Look for the Step 3. People think of experimental teams as the ones that build Gmail or Android, but they're more the ones building Gemini. It also happens quite early on, maybe as early as Series B companies.
You might want to avoid 'toy' teams. Gmail was probably the most successful toy project, but they're very rare.
One example is a product that has lots of TPV/GMV - payment gateways, marketplaces, listing sites. This usually doesn't translate to revenue/profit, but they're in a good position to sell things that are profitable.
Another is fixing problems in scale. Like FB was built on PHP which wasn't enough, so they ended up building Hack, React, a bunch of mobile stuff.
Some of the work is to build features requested by the core. An elliptical example here might be if you were Rolls-Royce and needed a specialized exhaust system, the specialist team would build it and then try to mass produce or sell that exhaust part to other companies.
There's going to be a lot of failed products and that's okay. The fail rate is usually higher than the core product, but lower than startups, so it's ideal for former startup folks.
I am saving money around the household by using media applications I wrote for media playlists, asset management, server management and dashboard, and more. Why pay for app store nonsense or subscriptions when I can do it better myself and with greater flexibility/durability.
That's interesting. How much do you save per month?
I am not really sure. It negates me needing to subscribe to all audio services and some video services. I don't need to buy corresponding media apps for my iPhone. The internet can go down and my stuff will continue working just the same on my home network.
I think I spend about $60 per month on streaming services. How many hours are you working on these projects because it may be more beneficial to do a few hours of consulting rather than saving a few dollars here in there.
I didn't think about explaining the obvious right away, so putting a comment here. Having a 'regular' job of a manager or a software engineer is fine but feels like I am not using most of my skills and not developing as a person. So the question really is how to apply this broad skillset to the world without getting into the confines of typical SWE roles.
Sounds like you should do some reflection and evaluation on the emotional side of things. What part of your dream of being an entrepreneur actually sounds good to you? If you want fame, software entrepreneurship may not be optimal for example.
Ultimately a job can be evaluated as: ( Money * Job Satisfaction * Impact ) / (Time * Energy )
Thanks for the question. I believe it's impossible to answer once and for all.
Currently, I like doing many things, finding the bottlenecks, and overcoming them. Today it's demand generation, tomorrow it's product and tech, and ultimately it's me being inadequate in some capacity. Which means lots of growth as a person, which feels very real, like you can be shy of being in front of another person and therefore avoid doing sales calls. This is big and feels much more real than 'growing' in an organisation where you're told to do XYZ to impress your manager so that they can beg their managers to get you into the raise quota, or even worse, simply bang your head against the 'we don't have money now' wall at a typical smaller company.
Being in control, jumping on interesting things to constantly learn something new and stuff like that are a good bonus as well.
I'm really similar to you. I could've written this post. You might have ADHD, at least subclinical. I know I have it. I don't see it as a disorder but as a difference - in my case that is (given that it is subclinical). Sometimes the difference is empowering, sometimes it isn't.
What you could do, if money is not too much of a concern: job hop to different jobs. I'm currently re-entering the job market as a data analyst. I've been a SWE for 4 years. I might get back to it (probably on the data science or data engineering side) but man I'm happy to have a different task set for the next 2 years.
Companies don't want all of your skills. They want a specific subset. You need to do things outside of your 'role' to grow.
Broad skill used for innovate/invent something but not make money.
If you want to make money, you should focus at 1, narrow. You need broader vision to find opportunity to make money on 1.
My specific advice for your situation, From easiest to start, to hardest:
- Immediately change work hours, work 4 x 10 hour days, if you can handle it. Can be tough for some.
- Go partial part-time, work 4 x 8 hour days, or 3 x 10 hour days (recommended)
Now that you've freed up your time, build!
DO NOT STOP YOUR DAY JOB, YOU WILL JUST BURN THROUGH YOUR CASH AND BE UNDER IMMENSE STRESS TO DELIVER. THIS IS NEVER THE RIGHT ANSWER, UNLESS YOUR PROJECTS ARE MAKING MORE THAN YOUR DAY JOB.
DO NOT DO PART TIME WORK ON TOP OF FULL TIME WORK. YOU WILL JUST BURN-OUT, DO WORSE AT YOUR JOB, AND HAVE NO ROOM TO THINK ABOUT PROJECTS. YOU NEED TO DROP THE FULL TIME WORK. SIMPLE AS THAT.
NOW, Build stuff YOU need, or your FAMILY needs
- Build stuff YOUR job needs. Follow the same advice as above.- Build simple MVPs, have a very fast feedback cycle: - Build MVP -> get feedback -> apply feedback -> get more feedback ...You mention your skillset is broad. Go DEEP in 1 or 2 areas in 2025. Stop having shallow knowledge, because your ideas will remain shallow if you don't address this. You do Software already, why not focus on 1 or 2 particular areas this year, with your newfound free time? Eg heres some areas I've thought up just now for you:
- Cybersecurity - Implement OWasp top 10 tips for Wordpress sites (developed as a wordpress plugin, or site, or browser extension etc)
- Backend - Build tools for API management, API testing, API benchmarking, API mocking, containerization
- Frontend - focus on UI, or UX, or accessibility, or performance, or a specific framework
- Frontends for firmware - hone your C/C++ skills and build simple frontends for users to configure hardware devices (Raspberry PI, STM32, ATMega etc)
- Browser extensions - Bothered by how websites look/feel? Bothered by cookies/privacy/lack-of? Bothered by ads/popups? Paywalled sites? Want Reddit to look better / more custom? Build a browser extension/s to address these issues. They are very easy to start, and cost nothing to run.
- IDE extensions, build extensions/themes for VSCode etc. Very easy to get into.
- Command line - did you know a group of people are making 6 figures selling coffee via SSH only?
- Graphics/gaming - Why not explore low-level graphics? How about Game development? Asset Pipelines?
- AI/Machine-Learning - Play around with some LLMs. Combine them with one of the above areas (eg browser extensions)