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throwaway342110 commented on Ask HN: How do you deliver big projects as a solo contractor?    · Posted by u/throwaway342110
jonahbenton · 6 months ago
It really depends. Every non-trivial organization has strategic needs the satisfying of which extend into years-scoped timeframes. These needs are intended to be realized by initiatives, which can be broken down into programs and programs into projects. Projects will be order months, a program might be multiple projects in a year, initiatives likely span fiscal years.

So- in terms of having stuff that needs to be done that takes a year or more- yeah, every organization has those. Is it common for there to be one thing that one contractor works on all by themselves that spans a year- sure, less than it used to be, not uncommon, but it speaks to a certain tempo and/or oversight culture that one has to be careful about.

It would be useful for you to understand, from the higher level planning perspective the organization has- why would this be shaped and scheduled this way? Sometimes these things are little white elephant or skunkworks projects that an exec wants to get done but has to keep on the downlow...could be any number of things.

The reason to understand that stuff is because it kind of becomes a risk to you, because these kinds of unusually shaped things also get cancelled all the time, for all sorts of reasons. If you put all your eggs in this basket and then things change- whatever the language of your agreement, you're potentially left high and dry.

So- even if as you are discovering more and making plans and so forth and it all seems good, it's a year or more, makes sense for you alone to do it, etc- still, you want to break down the work into phases (project scoped units), and report on those phases and on the larger phase plan. What you don't want is someone 6 months in poking around being like- what the eff is this? 6 months delivering nothing? What are we doing here?

throwaway342110 · 6 months ago
Thanks for your insightful answers!
throwaway342110 commented on Ask HN: How do you deliver big projects as a solo contractor?    · Posted by u/throwaway342110
jonahbenton · 6 months ago
What you are actually talking about is a situation where you have moved higher up on the consulting value chain. Your client probably has trust for you and almost certainly does not understand that the thing they want you to do, in the way you understand it, would take 2 years. (A SAAS play almost certainly has to have something out in the market in 3 months, from a business perspective.)

Moving higher in the value chain means instead of you doing things that the client well understands the dimensions of, you are now doing something they don't understand the dimensions of. This is a critical and risky point. If you dive into implementation, they are going to be unhappy.

To serve them well, you have to now understand what they do not understand, and what is actually important to them. Almost certainly timeframe is important, but there will be a nuanced balance between 3 points of the triangle- time, features, cost- and you/they can only control two. The third is dependent on the others.

Upon eliciting more about what is actually important about the business context and opportunity, you help them most by presenting a strategy that incrementally and sufficiently delivers what is most important to them in the order of importance in the timeframe that matters.

Whether or not they know it, this is a strategic planning engagement first, before it is a implementation engagement.

And maybe you learn that cost is not an issue, they have critical needs in terms of features and time, so- you or they need to find additional resources and then manage them through implementation. Acting in a program management capacity over additional resources brings its own challenges, and it brings its own benefits. This is the transition from solo contracting to consulting. This profit margin on less expensive resources' time is how the money is made in consulting.

HTH.

throwaway342110 · 6 months ago
Thank you! That makes sense. The client does have some understanding about the scope of the project, since when he approached me he stated "I'm not sure if it's something for 1 person", but yeah, the timeframe would probably be an issue and I need to push it to cut it to the essential features first and add anything non-critical later.

However, is a 1 year timeframe something common / acceptable in the industry? I don't think everyone is hiring sub-contractors and it's rather hard for one person to deliver anything substantial in 1 year unless they work overtime like 50 - 60 hours per week.

throwaway342110 commented on Bootstrapping a side project into a profitable seven-figure business   projectionlab.com/blog/we... · Posted by u/jonkuipers
bravesoul2 · 7 months ago
For me the lesson is: ship the thing that makes you feel like you are playing Golf doing it (assuming someone who plays Golf enjoys it alot).

The golfer won't regret their day on the course. And if you fail on the passion project it won't feel like a fail.

I have another idea too. It's the win anyway system. Pick something that if you fail you use those skills at work and get ahead. E.g. the side project is also the training for the gap in your career.

throwaway342110 · 7 months ago
This is my plan now, launch a free product and use it to promote myself as a contractor or consultant. Commit to some time spent on maintenance weekly and consider it as part of the marketing time. Maybe I will be able to monetize it in the long term, but in the short term, I need it to escape the bottom of the barrel I am currently at. You don't get to have a good resume when you are tinkering with products on your own... and I realized that especially in this job market, I can only make decent money on my own. It helps that the product is quite technically complex, gives me ideas for blog posts and the idea itself is already validated (as a free product), but the existing implementations are poor. And I absolutely love developing it.

The big lesson for me is know what you are getting into. Look at the OP - he spent every spare hour he had. This is no joke. I have done something similar in the past for a time and I ended up constantly running into conflicts of priorities between that and personal life. I ended up wasting a few years, in both personal life and professional life, although the former hurts much more. This is how I ended up in a scenario where I have nothing to show and nothing to lose. I just hope I can do it all at some 50 hours per week total, where the product is just a part of the day job (promotes the consulting offering) and lower the volume of paid work as I need, if I want to have more time to make a big move with the product.

u/throwaway342110

KarmaCake day3July 10, 2025View Original