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Ask HN: What mistakes did you make when starting as a consultant/freelancer?

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Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#11

Hire a good tax person immediately. Maybe hire 2. A significant amount of your income earned is gained through having someone walk you through handling taxes & health insurance. I'm not suggesting cheating on taxes. There are common practices such as knowing how to best incorporate your business for your situation. How to best pay yourself (dividends vs income) & how to handle your personal & company expenses. This c…

What country are you basing this advice on? I think it’s good advice, but if your income can increase by 20-30% as a result of optimising your business structure for tax purposes, that’s a dysfunctional tax system. I’d like to believe that in some countries this advice is not necessary.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#12

Setting my rates too low. Here's what I figured out those many years ago. Clients who are cheap are also really into wasting your time and trying to micromanage the project. Clients who will pay a lot more also give you latitude to do your job (after all they're paying you to be the expert). Keep jacking up your rates with each new client until you hit a ceiling. Whatever you're charging now, without even knowing wha…

I can second this piece of advice. When I first started our small consulting firm we didn't know how to scope explicitly enough and didn't charge enough even if the projects did stay within the scope of work.

Don't be embarrassed of your rates. If they're flirting with but not plainly past what potential clients are willing to pay, you're in/around the right territory. Additionally, explicitly the definition of successful deliverables in your SOWs - make sure that you get enthusiastic client sign-off on these criteria. This can only serve to make everyone better off when work is marked as complete.

Last, "Due on Receipt" with some understanding and grace is a lot better than having to send "Hey just wanted to check in about invoice #1113" emails 10 days after your 30-day receivables haven't come in.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#13
post #8

Hire a good tax person immediately. Maybe hire 2. A significant amount of your income earned is gained through having someone walk you through handling taxes & health insurance. I'm not suggesting cheating on taxes. There are common practices such as knowing how to best incorporate your business for your situation. How to best pay yourself (dividends vs income) & how to handle your personal & company expenses. This c…

What are some ways to (a) tell a good tax person from a bad one and (b) look for a tax person in such a way that increases your odds of finding a good one?

I found my tax person through a referral. Went in and chatted with him about some questions and that was that. 15 years later I still use him, though I don't consult any more.

This points out another good tip: find a network of other software consultants that you can trust and ask questions of. I found mine, years ago, by keeping in touch with past colleagues; some of them had gone independent. Now I'd probably look on a local slack and organize a few lunches.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#14
post #11

Hire a good tax person immediately. Maybe hire 2. A significant amount of your income earned is gained through having someone walk you through handling taxes & health insurance. I'm not suggesting cheating on taxes. There are common practices such as knowing how to best incorporate your business for your situation. How to best pay yourself (dividends vs income) & how to handle your personal & company expenses. This c…

What country are you basing this advice on? I think it’s good advice, but if your income can increase by 20-30% as a result of optimising your business structure for tax purposes, that’s a dysfunctional tax system. I’d like to believe that in some countries this advice is not necessary.

I run a small consulting firm in the United States - you can definitely goose dollars-in-pocket based on your type of consulting and other arrangements.

Imagine that I run two firms - one that provides primary top-level advice, guidance, etc. here in the states, and with the other doing some or all of the implementation work in a U.S. territory like Puerto Rico. Much of the profits can end up in PR, and when your continental entity needs cash it can borrow it from your PR-entity at a decent interest rate to further reduce states-based taxable income. You don't really even need to be a citizen of PR for that to begin working. That's one of innumerable ways to reduce your tax burden here. An ambitious accounting and legal team can help you ensure that you keep as much of your total billings as possible.

We don't do this - we're too small and due to ambitious growth we end up eating most or all of our earnings each year anyway. Definitely seen it before.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#16
1) I thought that getting clients would be relatively easy, but getting new ones is more about trust than anything else. I moved back to my home town after spending two years away and noticed that my professional network there was quite poor so it took awhile to find a gig (~2 months and it's not in my home town).

2) When looking for opportunities (any kind really), the 80/20 rule applies. Try to focus on the 20% that produce 80% of the results. In our case we started by cold contacting, with quite poor results. Instead, we've been pretty successful using local freelancing networks/sites ran by larger consultancies to outsource the work they don't have the resources to do. Granted that's just subcontracting but it's a decent way to start out. I'd imagine the way the 80/20 rule applies when building direct client relationships is to focus on large-ish corporatios with decent financials that are already using contractors.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#17

There is an excellent book that I would suggest called “The Secrets of Consulting” by Gerald Weinberg. I also use a tool called FreshBooks that has been killer as far as invoicing and tracking time.

Happy ex customer of Freshbooks (ex because I am no longer consulting). I will say if you are disciplined and want to save every penny, you can get by with Excel and word for invoicing, but once you get your first client or two, Freshbooks is real nice to have. Easier, invoices look better, you get reporting.

And the Weinberg book is top notch. Anyone who wants to solve problems in business should read it.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#18

Not billing often enough. Send a bill every 2 weeks. If they miss one, stop working. No negotiations.

Agreed! And send the initial bill after the first week to familiarize the client with your invoicing process. (They typically appreciate this.)

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#19
post #11

Hire a good tax person immediately. Maybe hire 2. A significant amount of your income earned is gained through having someone walk you through handling taxes & health insurance. I'm not suggesting cheating on taxes. There are common practices such as knowing how to best incorporate your business for your situation. How to best pay yourself (dividends vs income) & how to handle your personal & company expenses. This c…

What country are you basing this advice on? I think it’s good advice, but if your income can increase by 20-30% as a result of optimising your business structure for tax purposes, that’s a dysfunctional tax system. I’d like to believe that in some countries this advice is not necessary.

Apologies. I should have clarified. United States of America.

I don't believe it's dysfunctional for this particular reason. There are for sure trade-offs between simplification & trying to optimize for the best outcome. A simpler tax code would be nice but then people on all sides of the political aisle would start saying we should really give X a break for Y reasons and that's how it seems to get complicated.

There is literally a 20% tax break for most small businesses this year in the US.

Healthcare can be cut in half if you are below certain requirements but make a $1 more & you pay the whole bill. This one I agree seems silly. Though it's maybe to simplified & should be more complex with a sliding scale.

A popular move for freelancers is to start an S-Corp LLC where you pay yourself a fair wage compared to others in the industry. This money gets taxed hard. Harder personally for you than if you worked for someone else. You can pay yourself dividends though with any extra money your earn as long as it's less than your wage income. This money gets taxed much less.

How you invest your money is also taxed all sorts of different ways.

Note - I'm not a tax professional & the above is just my understanding. Someone who is a professional or has more experience would give better advice hence my original post.

Re: Ask HN: What mistakes did you make when starting as a consultant/freelancer?

#20
I tried freelance and realized I hate it more than any other type of programming work.

I can tolerate being an employee where I do what I'm told. After a month I get a feel for the environment so it becomes low stress and then I can keep my head down programming. Or I can tolerate selling software or having a SaaS. If I'm CEO I decide the direction of the product and then just have to handle customer support.

But the BS and stress of dealing with clients, contracts, undefined specs and getting paid... I have no f-ing idea how people tolerate it. So good luck with that. It took me way too long to figure out that I absolutely hate working as a contractor.

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