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Comment by seangrogg | Hacker News Reader

For those interested (namely, me) could you describe your current situation?

* What sort of business entity are you using? What considerations did you make when choosing this entity?

* What is your work like? Are you remote/onsite? Do you have one client or multiple?

* What is your staff like? Are you a lone worker? Do you have coworkers in your business? What did you choose to offload onto others?

* How do you manage taxes, insurance (beyond those covered by your wife), and finances?

* What alternatives have you considered in the event that your wife couldn't cover you?

Mostly interested because this seems like a viable career path (to me) but I would definitely want to consider it with eyes wide open and learn from someone else's successes and failures.

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I've been doing contract work since 2004

* LLC with S-Corp designation. This is very tax-advantaged vs. Sole Proprietor.

* Currently, I'm mostly on-site for one client.

* 1-person shop.

* I have an accountant. You want a good, small business accountant.

* I buy health insurance for my family through the ACA exchange. It's very expensive so make sure you factor it into your rate.

I've had 2 FT gigs that lasted 6 months each since 2004 and regretted it both times. If you can handle having to network and interview frequently you can make more money with more flexibility as a contract developer.

Thank you very much for the insight! A few questions, if you would:

* What are some recommendations you have for establishing a rate? Do you use hourly, weekly, or project?

* What do you look for in a small business accountant (it sounds like you may have had a less-good one in the past)?

* What avenues do you typically find yourself using for contract work? i.e. LinkedIn, job boards, word of mouth, etc?

* I use hourly mostly because it is common and is met with the least resistance. Either way, raise your rate at least a little after each gig. Don't get complacent, just keep ratcheting it up.

* I've actually been blessed with a great accountant. He's saved me thousands over the years and sent letters to the IRS on my behalf clearing up a couple issues along the way. I would look for someone who specializes in small, professional service firms that is used and referred by people in your area. If they tell you they don't think you should organize as an LLC, look elsewhere.

* Starting out I used recruiting firms. They have the advantage of an established network and getting you paid every 2-weeks. The disadvantage of course is they take a cut. Their first ask will always be a low-ball hoping they can get a huge margin. Always try to get them to make the first offer and always ask for more. You'd be surprised how much room they have to negotiate up most of the time. As I've made connections over the years I've relied more on my network, but I'll still use an agency to fill the gaps. Also, boutique consulting agencies can be great for sub-contract work. They often need to staff up for a project they just landed, but don't want to take on full-timers and they usually command excellent rates.

Awesome! Thank you very much for your time and answers!

> boutique consulting agencies can be great for sub-contract work

I just wanted to second this point. In this way, checks both boxes off: one for getting the advantage of an established network like a recruiting firm; two for getting you the higher rates and not needing a middleman

* Currently sole proprietor. Will switch to LLC or C Corp in 2018 (depending on income), but I'd talk to your accountant to find out what's best for you.

* I'm remote currently with high utilization client (as a subcontractor) and smaller retainer clients.

* I am a firm of 1.

* I have an accountant to manage taxes and finances. I keep meticulous records of what is a business vs a personal expense. The subcontractor gig is insured by the main contracting company. The retainer gigs stipulate it is knowledge/access only, so without any IP deliverables required, so there's no need for insurance on that. I may get insurance if my employment situation changes in terms of the contracts I take on. For this, I'd talk with your lawyer.

* I would just buy health insurance through the state. I live in MA, so we have to have something. We're both young and healthy, and she has an incredibly stable job, so I don't worry about this one too much.

I should point out that I'm very new to this (4 months in) so definitely don't look at me as a source of having "done things right" - I am learning every day and still sweating it all.

Very interesting. Thanks for being candid with your freshness to this experience; it's valuable all the same. A few more questions, as your availability permits:

* Have you considered an S-corp? If so, reasons against listing it as an option?

* Any recommendations in general contractors (even if not specific ones, just things to look for in a general contractor)?

Thanks for your time and response(s)!

* I haven't considered it, I just do what my accountant advises

* A general contractor? I hear that term I think of those guys who work on your house. Could you be more specific?

* fair enough

* I guess I just lifted the term as it seemed appropriate; given you mentioned subcontracting I imagine there is an entity above you that does the direct contracting - any recommendations for what to look for in that contracting authority?

Good marketing. They came to me

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