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> "No one really explains to you taxes and contracts and how to chase a client for that bill that they owe you — like, the nitty-gritty," Wait...what? Before

> "No one really explains to you taxes and contracts and how to chase a client for that bill that they owe you — like, the nitty-gritty," Wait...what? Before I even broke out into freelance consulting I hired an accountant. When starting your own business, I would think it's base-level knowledge that anything with legal ramifications (and that includes the IRS) should be handled by a professional. Get an accountant. Get a lawyer (at least for one day to draft up your documents and make sure your business is set up or even use LegalZoom). And within the first month of breaking out on my own, I must have read like 3 or 4 books on freelancing/consulting, 10+ blog posts, and podcasts. True - no one is going to act like Clippy and say "Hey looks like you're starting a freelance career. Have you considered an LLC and liability insurance?" But - do people not try and learn about what they're getting involved with anymore? Starting a business, even if it's a 1-person sole proprietor consulting firm, is a big task. And yes, davidscolgan is right that you should consider all business aspects beyond your primary skill. But it seems almost irresponsible to say that starting a business is going to be a huge shock. No one is going to tell you, but even a cursory search online will give you a torrent of information on freelancing, consulting, and starting your own business. If I hadn't put in the initial legwork into studying the consulting landscape there is absolutely no way I'd: (A) still be consulting or (B) make nearly as much money. But the answers are out there. And yeah - get an accountant, it will drastically simplify your finances.

rietta 8y ago
Some people down on their last $100 or less don't always have the luxury of choosing. Building a Wordpress site NOW for a little money or doing something in PHP/MySQL today if you have some basic skills and next thing you know, you're a freelancer without the luxury of having planned all that up front.
rietta 8y ago
That said, I never really found taxes all that confusing even long before hiring an accountant. Turbo Tax was always easy. I did have the advantage of learning from my grandmother (who was a bookkeeper) and my dad who was an executive as I was doing my first business as a teenager.
cgb223 8y ago
> And within the first month of breaking out on my own, I must have read like 3 or 4 books on freelancing/consulting, 10+ blog posts, and podcasts. Any recommendations?
- oneredoak 8y ago
  Brennon Dunn has a lot of great free blog content and an excellent podcast about all things freelancing / software consulting. Would highly recommend as his content has helped me a lot over the past year, mainly regarding the marketing/selling, billing and dealing with clients sides of things: https://doubleyourfreelancing.com https://doubleyourfreelancing.com
  - SyneRyder 8y ago
    Brennan Dunn's stuff is great, and I know freelancers who have been very successful in part thanks to him. I'd recommend starting small if buying products though - he had a $50 book version of Double Your Freelancing that was worth it, but at one time he also had a $2000 online course version which probably isn't the right choice for everyone. Freshbooks have a fantastic free PDF called Breaking The Time Barrier that is about charging for value, not for your time. It's worth reading even if you don't use Freshbooks (I use Harvest instead). The PDF was actually recommended to me by a client, who I think was giving me a hint that I was charging unsustainably low prices. https://www.freshbooks.com/blog/breakingthetimebarrier https://www.freshbooks.com/blog/breakingthetimebarrier
graeme 8y ago
This is far outside the norm, in my experience. At least for people under 30. Maybe seasoned business savvy professionals who start later are different. But I've had to do a LOT of coaching whenever a friend starts freelancing. Even basic stuff like "a separate card for business expenses can simplify your life" And these people usually do well. It's just that most people have no clue about even basic business stuff, and nor do their families or social networks, so no one tells them. Did you have experience in a company, or a friend relative who had told you about business before?
wanderingstan 8y ago
It's great that you did that, but in my experience (and many freelancers I know) there was not a definitive "I will now become a freelancer" moment. I had moved to a new city and was interviewing around. A old friend approached me in desperation, offering a lot to work on one-time project for his company. That led to more offers, and those to more. Meanwhile I and friend were building prototypes around a business we might start. (So glad we didn't try to start that one!) Meanwhile, it wasn't until I did my taxes the next year that it hit me that I was now a freelancer. Only then did I start to get my act together with billing and the rest.
mwexler 8y ago
"If I hadn't put in the initial legwork" might better be read as "If I hadn't invested up front in some startup costs from experts who know things I don't". Paying for Lawyers and Accts seems crazy, when we have the web and a local library. But it often turns out to be 50% wasted money... and 50% "saved my life" money. After all, an entity is hiring _you_ because you have skills they can't do even though there are tons of books and sites on dev and web engineering. It's wise to do the same yourself for the skills you don't have, or don't have time to master. BTW, I found lots of variability in pricing around lawyers and accountants, and some negotiation can go a long way.

rietta 8y ago

Some people down on their last $100 or less don't always have the luxury of choosing. Building a Wordpress site NOW for a little money or doing something in PHP/MySQL today if you have some basic skills and next thing you know, you're a freelancer without the luxury of having planned all that up front.

rietta 8y ago

That said, I never really found taxes all that confusing even long before hiring an accountant. Turbo Tax was always easy. I did have the advantage of learning from my grandmother (who was a bookkeeper) and my dad who was an executive as I was doing my first business as a teenager.

cgb223 8y ago

> And within the first month of breaking out on my own, I must have read like 3 or 4 books on freelancing/consulting, 10+ blog posts, and podcasts. Any recommendations?

oneredoak 8y ago
Brennon Dunn has a lot of great free blog content and an excellent podcast about all things freelancing / software consulting. Would highly recommend as his content has helped me a lot over the past year, mainly regarding the marketing/selling, billing and dealing with clients sides of things: https://doubleyourfreelancing.com https://doubleyourfreelancing.com
- SyneRyder 8y ago
  Brennan Dunn's stuff is great, and I know freelancers who have been very successful in part thanks to him. I'd recommend starting small if buying products though - he had a $50 book version of Double Your Freelancing that was worth it, but at one time he also had a $2000 online course version which probably isn't the right choice for everyone. Freshbooks have a fantastic free PDF called Breaking The Time Barrier that is about charging for value, not for your time. It's worth reading even if you don't use Freshbooks (I use Harvest instead). The PDF was actually recommended to me by a client, who I think was giving me a hint that I was charging unsustainably low prices. https://www.freshbooks.com/blog/breakingthetimebarrier https://www.freshbooks.com/blog/breakingthetimebarrier

graeme 8y ago

This is far outside the norm, in my experience. At least for people under 30. Maybe seasoned business savvy professionals who start later are different. But I've had to do a LOT of coaching whenever a friend starts freelancing. Even basic stuff like "a separate card for business expenses can simplify your life" And these people usually do well. It's just that most people have no clue about even basic business stuff, and nor do their families or social networks, so no one tells them. Did you have experience in a company, or a friend relative who had told you about business before?

wanderingstan 8y ago

It's great that you did that, but in my experience (and many freelancers I know) there was not a definitive "I will now become a freelancer" moment. I had moved to a new city and was interviewing around. A old friend approached me in desperation, offering a lot to work on one-time project for his company. That led to more offers, and those to more. Meanwhile I and friend were building prototypes around a business we might start. (So glad we didn't try to start that one!) Meanwhile, it wasn't until I did my taxes the next year that it hit me that I was now a freelancer. Only then did I start to get my act together with billing and the rest.

mwexler 8y ago

"If I hadn't put in the initial legwork" might better be read as "If I hadn't invested up front in some startup costs from experts who know things I don't". Paying for Lawyers and Accts seems crazy, when we have the web and a local library. But it often turns out to be 50% wasted money... and 50% "saved my life" money. After all, an entity is hiring _you_ because you have skills they can't do even though there are tons of books and sites on dev and web engineering. It's wise to do the same yourself for the skills you don't have, or don't have time to master. BTW, I found lots of variability in pricing around lawyers and accountants, and some negotiation can go a long way.