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All business is non-trivial, else more people would be doing it!

I've been freelance and/or doing start-ups for ~30Y. There's always something difficult, but sometimes it at least turns into a great war story. B^>

Adding more people to the mix, unless you are a good manager or hire one, isn't likely to make things easier.

I've addressed a few of the issues you're having on my freelancers blog at https://medium.com/workroll

Here's some quick pointers...

1. Automate your lead generation. shameless plug: https://workroll.com

2. Don't estimate or provide hourly quotes. Use fixed prices based on value you're providing.

3. I literally have a list of 100 places to find clients... https://medium.com/workroll/find-5-freelance-design-developm...

4. Immerse yourself in their business, ask lots of questions and find out where their problems lie. Then charge for fixing them.

5. Contracts are useless if you can't enforce them. Learn to spot bad clients and avoid them, charge a deposit, and break work up into milestones. More here: https://medium.com/workroll/8-red-flags-to-avoid-bad-freelan...

6. Writing software is getting easier, sorry you're just wrong on this one!

P.S. hiring a sales person won't work. You are the best sales person you can find.

> Both require estimating, which I feel like I'm getting worse at. The unknown unknowns kill my schedules.

Generally what I do is break the project down into a list of small tasks, then estimate the best possible case and the worst possible case for each. Unknowns and more people involved increase the worst case. Try to ask more questions to reduce the unknowns but after that you have to keep your worst case estimate in mind.

Why do you feel you're getting worse at it? You're always going to finish slightly above or below your estimates. If you're consistently too low though you're being too optimistic when estimating and should adjust, and/or you're not pinning down requirements enough.

I feel like I'm getting worse because some of my project surpass my worse-case. All things being equal, the project I'm thinking of involved working with new technologies.

So perhaps the lesson there is to apply an appropriate coefficient according to how well I know the technology.

Been there, burned out, got very corporate-sick.

Now I'm trying to break my services into highly specific niche jobs, things you can do in just 1 or 2 days: Fewer responsibilities, almost no sale cycle, fixed price, advance payments, easier to make the client happy and, most of all, the rediscovered joy of doing what we really like to do, solving problems.

You still have to market your service, but it's easier to sell since it's supposed to solve a very specific problem.

I’m interested in what kind of problems you are solving for your clients.

I always thought complex/fun problems take a bit longer. That has some disadvantages though: the longer you work for a client, the more knowledge you have. You may end up having the responsibility to keep supporting whatever you implemented. In my case you then end up with a few bosses (instead of one boss as an employee). I would much rather go in, do the job, and get out again.

I too am very interested in the kinds of niche jobs you do. Or rather how I might be able to break down what I do similarly.

Find a niche is the hardest part, indeed. Some people call it “Positioning”. Well, I don’t think it’s useful for you what I’m currently experimenting with, I bet it’s far more interesting how I found it.

I will share some thought that helped me a lot, your mileage may vary:

1) Think about something you can do really well, and that you can do in 1 day. Look at your past proposals, find that single task where you think you can make a difference or remember that problem you solved so elegantly. The “1-day” thing is completely arbitrary but keep in mind that the shorter it is, the better chances you'll have to test and sell it.

2) The task should be something that a fair number of people need (even if they don’t know it yet). Listen to your clients, try to remember what they asked more often in your past projects. Listening and frequency are key here.

3) The task doesn't need to be anything extra innovative or super revolutionary, actually, it should be something very simple. Think small! For me, the biggest challenge was to fight my own ego. I think I’m very good in some areas of my expertise. In 10+ years of freelancing, I ran this race to the bigger project, the bigger client, the bigger challenge, the bigger reward. At some point, I had problems explaining why my solution was so much better and the best one for the client, who only wished someone solved his silly problem and didn’t give a damn about it, best price aside. Remember, burn out come mostly out of frustration. I felt I was tricked into playing the wrong game. Then, I found that bigger isn’t always better, many times it is just… bigger. Again, this is just me with my own story and my own experience, your situation may be different.

4) Once you find it try it out. Fast. Share it with your clients and colleagues. Make a 1-day mvp or landing page and throw some Adwords on it, leave the details for later. Don’t overthink it, don’t overdesign, don’t over-engineering, don’t over-anything, just test your idea. My rule of thumb is that if something works, it will work since day one. At least you will receive some genuine positive interest almost immediately.

Other notes:

- You will still do freelance work on ordinary projects. Your idea will act as a bait, some clients will be very happy and will ask you to solve more of their problems. Hopefully, this time it’s in your hands to choose the right project and the right client and not the other way around.

- Again, you will also find ways to upsell more complex solutions with the right clients.

Well, I think I'll stop here, sorry, if I had more time I would have written a shorter comment. Just hope some of this will help.

Like the others, I'm curious as well. It would be great to have a model like that, at least it sounds like it at this point. :)

One word: Sub-contract.

Network with small to mid-size consulting companies. If they can trust you, it's a win-win. You 1099 with them, they make $20-$30+/hr off the top of your rate w/ no burdens of having you as an employee.

This also removes the complications of the sales side of things.

A lot of what you're talking about sounds familiar. It'd be nice to talk to someone, even if just to commiserate and bounce ideas off each other.

My email is in my profile, if you're interested. Good luck.

Sounds like you know what you are doing so either you're a bit unlucky or this is typical for the freelance industry.

I suspect you're not alone.

Start to think of investing part of your time in building a side passive income project that can grow...

For what it's worth

1, drop the hourly rate, all you do is price yourself out of work. As an example, a great programmer can do it in 1 hour, a medium programmer can do it in 2 hours, an average one can do it in 3 hours etc. So the better you are, the less you actually get paid. Obviously you can raise your prices to compensate but then people will just go to a cheaper developer and probably end up paying more without realising it. So drop the hourly rate.

2, isolate yourself from the clients, coding is fun, clients are hell. Get a sales person in to do that stuff for you.

Dropping his hourly rate will likely get him more of the kinds of clients that he does not want. Your advice goes very much against the grain of what others who are very experienced in this field would say (which is to raise your rates).

What is your basis for suggesting he lower his rates?

He's not saying lower the rates. He's saying charge by the project or by the week/month, not by the hour.

I'd also suggest daily rate or weekly rate as alternatives. Seems like a better unit to bill consulting services in than hours or months. Easier to sell clients 20 days of your time or 4 weeks of your time imho. It is easier for companies to budget x days or x weeks of consulting services with fixed daily / weekly rate.

I didn't say for him to lower his rates. I said for him to stop charging by the hour, charge by the project instead. An hourly rate is a fundamentally broken system.

Charging fixed price per whole project might not be a good idea. Software projects usually never finish completely in a certain predefined deadline so it makes it very hard for you to plan and price your services.

There will always be issues that will delay the project that you couldn't have predicted and priced in at the start, requirements will often change during the project, there can be new feature requests which will further push the deadline.

Much better to instead sign a contract for fixed amount of time (6 months of consulting services for example). You will work on the project for the time defined by signed contract.

A month before your contract ends sit down with the client and estimate the current state of the project and see if additional time will be needed in which case you can negotiate contract extension. This approach is much more agile actually so most clients would prefer it I'd imagine.

Clients can keep extending your contract by 3 month chunks if they need to. If you finish everything early clients will easily find you some more work while they are paying for your consultancy services. If not you can have short notice period in the contract like 1-2 weeks so contract can be cut short.

I've tried fixed bid. However, whenever I do a fixed big project it takes longer than I expected and it ends up costing me. Obviously that means I'm under-estimating and/or not charging enough. Or perhaps it means the way I come up with the fixed cost is wrong.

Generally, I break the project down into a list of tasks. Estimate liberally for each task, then multiply the final number of hours times 2 then multiply by my hourly rate.

To your second point, as a small 1-2 person company, how could I afford a sales person? Are there sales people out there who would purely work on commission?

Try daily rate. Say you charge $800 per day. Minimum charge is one day. If you do work in 2 hours it doesn't matter because you'll charge full day as it's inefficient use of your time to split it into minuscule hourly chunks.

And don't do small projects which take couple of days or weeks to finish. Try to get commitment from clients for at least 3-6 months of work. So get a written contract which defines your pay to be 22 * daily rate * number of months, billed weekly let's say.

You'll have much less stress and waste less time looking for new clients.

Basically I'm suggesting you become a contractor with a daily rate, work on projects which last around 6 months on average per project. You can then slowly transition from this to more niche or specialised consulting. And you'll have a decent Rolodex of clients and references after contracting for couple of years.

Ask HN: At my wits end