4 ms·

Ask HN: Done with startups. Contemplating freelancing

21 points by consowels 12y ago

(I'm a semi-regular HN participant using a burner login to hide my identity.) I've spent all (15+ years) of my career at startups. Several times I've been a single-digit employee and have unsuccessfully founded a company. I've had one modest pay day but that money is long gone. I think I've had enough. I've grown tired of the ups/downs and long hours (50 to 60 hours a week.) My imagination is no longer captured by prospects of changing the world or a big pay day. I'm exploring the world of freelancing. I'm thinking I could work 4 days a week on average on paying projects (Ruby, Rails, iOS, C) and spend one day a week working on open source or other side projects (which may or may not generate revenue.) In general, looking for an environment where I have more autonomy and better work/life balance. Has anyone successfully made this kind of transition? Many thanks.

tptacek 12y ago
Yes. Keep in mind that the term "feast or famine" was invented to describe freelancing operations. At least in the first year or so, you're going to have very similar ups and downs to a startup. But obviously, the variance in outcomes for freelancers is lower than that of startups; you'll eventually get your sea legs. Successfully freelancing --- and you have to do it somewhat successfully to get to the place where you can set up your schedule like you want --- requires a lot of the business and sales skills that getting a startup off the ground requires. Friends who have tried to start freelancing businesses have washed out after a couple years because they just can't deal with the grind of selling.
- quizotic 12y ago
  I'll second this. In my case, fear of famine (which never actually happened) often led me to take on too much work to have a side project. Sometimes, I couldn't do as good a job on concurrent projects, but was afraid to do things sequentially or turn down projects. FWIW, the business and sales skills tptacek talks about end up helping when the startup bug strikes again ... which it probably will. It's been said elsewhere, but one of the most important things is to hold firm on price, probably a much higher price than feels reasonable coming from startups. If you're not charging by the project, charge by day, not by hour. You have extra costs as a freelancer, and you provide extra value. So build that in.
  - pjungwir 12y ago
    > fear of famine . . . often led me to take on too much work to have a side project. A model I really like is one "big" engagement at 20 hrs/wk and a few smaller ones to fill in the rest of the hours. This gave me a lot of confidence walking up my rate and saying no to discounts. Knowing I had stability from other relationships took away a lot of fear and let me be more willing to hold out for better opportunities.
- consowels 12y ago
  "The grind of selling" is exactly one aspect freelancing which I'm unsure I'm up for. I do understand it's necessary for this to be successful.
  - Mz 12y ago
    I do freelance writing, not coding. For me, a good service has been really helpful. The issue is finding a good one. So maybe look around for a service, try a few out, see if anything sticks. If not, you can email me and I can talk with you about my opinions about good vs bad services and if there isn't anything like it in the coding space, maybe you have your next start up idea. :-) Best of luck, whatever your future holds.
kohanz 12y ago
I've recently made a transition from full-time work to sparse, part-time freelancing, which I deem successful, but may not be by others' criteria. The parameters of my freelancing are undoubtedly much different from yours, but perhaps my experience is still of use. Up until May 2014, I was working FT at a small non-profit (government-supported) consulting firm in the medical devices space. At this point I had about a decade of progressive development experience and more than half of that in the medical space. I wasn't totally happy at that position for various reasons and, for some time, I had been interested in having more time to work on my own projects. Part-time work was what I thought I needed, but no employers were interested in that kind of arrangement. Also significant is that in April 2014, our first child was born and I knew that I wanted to be an involved parent. So as my son's due date came closer, I investigated freelancing as an option. Another factor that is important in my case is that due to my previous employment and my family's relatively frugal means of living, we are doing OK financially. We live in a medium-sized city in Canada where living costs are lower tha your bigger tech hubs. I knew that I could go a year or more with almost no income that we'd still be fine. I've come to realize that this is a blessing and a curse at the same time though ;) To be honest, some things just fell into place for me. One of the clients that I was the lead on at my day job was someone I knew that I could talk to openly and when I told them that I would be leaving, they showed immediate interest in retaining my services. My employer was fairly shocked at my leaving. I was (and I try to say this as modestly as possible) the most productive and reliable developer there and also the one trusted most with customer relationships. I gave them plenty of notice (6 weeks) and we left on very good terms. Here's the kicker, my old employer is now my #1 client. I am essentially a subcontractor to them. I make about 1.75x what I did as a FT'er on an hourly basis doing my old job for them, but I have the ability to set my hours, workload, and decide which projects I take on. It's almost funny to me because if they had offered me reduced hours and similarly reduced pay in the past, I probably would have taken it. I charge them a bit less than other clients, because they take the pain of finding new customers out of the equation for me. All this said, I bill about 50 hours a month. I could bill more (take on more work), but that isn't my objective. The other time I spend working on my startup and I spend an above average amount of time at home, being a dad. This is exactly the arrangement I was looking for and I couldn't be happier with life these days. This won't last forever. That's why I've got the startup in the works and also I know that, should I ever need, I have a reasonable number of contacts in my city to get another job (and I'm sure my old job would still be available should I choose to return).
larrykubin 12y ago
I successfully freelanced for years. I think one key for me was living in Austin, where there is no state income tax and the rent and food costs are low. It doesn't take many hours of consulting work to be able to live comfortably there.
MichaelCrawford 12y ago
This might help: http://www.warplife.com/jobs/computer/telecommute/ http://www.warplife.com/jobs/computer/telecommute/ I too am very skeptical of startups. I'd rather get paid by the hour, then get paid with a promise that's not likely ever to be kept. I understand one-half of American businesses - in general, not just startups - fail during the first five years.
- mod 12y ago
  Wouldn't these businesses all be startups? What is the differentiator in your mind?
  - MichaelCrawford 12y ago
    Some are startups but most of the companies I list are not. I spent quite a lot of time puzzling over whether I should reject certain kinds of companies from my list. In the end I decided that I would not, but I do plan to make it more clear that the user is advised to research the companies before accepting an offer, or even before applying. To make that easier, in the future I plan to link to the Better Business Bureau, Glassdoor and the Securities and Exchange Commission pages for each individual company.

21 points by consowels 12y ago

tptacek 12y ago

Yes. Keep in mind that the term "feast or famine" was invented to describe freelancing operations. At least in the first year or so, you're going to have very similar ups and downs to a startup. But obviously, the variance in outcomes for freelancers is lower than that of startups; you'll eventually get your sea legs. Successfully freelancing --- and you have to do it somewhat successfully to get to the place where you can set up your schedule like you want --- requires a lot of the business and sales skills that getting a startup off the ground requires. Friends who have tried to start freelancing businesses have washed out after a couple years because they just can't deal with the grind of selling.

quizotic 12y ago
I'll second this. In my case, fear of famine (which never actually happened) often led me to take on too much work to have a side project. Sometimes, I couldn't do as good a job on concurrent projects, but was afraid to do things sequentially or turn down projects. FWIW, the business and sales skills tptacek talks about end up helping when the startup bug strikes again ... which it probably will. It's been said elsewhere, but one of the most important things is to hold firm on price, probably a much higher price than feels reasonable coming from startups. If you're not charging by the project, charge by day, not by hour. You have extra costs as a freelancer, and you provide extra value. So build that in.
- pjungwir 12y ago
  > fear of famine . . . often led me to take on too much work to have a side project. A model I really like is one "big" engagement at 20 hrs/wk and a few smaller ones to fill in the rest of the hours. This gave me a lot of confidence walking up my rate and saying no to discounts. Knowing I had stability from other relationships took away a lot of fear and let me be more willing to hold out for better opportunities.
consowels 12y ago
"The grind of selling" is exactly one aspect freelancing which I'm unsure I'm up for. I do understand it's necessary for this to be successful.
- Mz 12y ago
  I do freelance writing, not coding. For me, a good service has been really helpful. The issue is finding a good one. So maybe look around for a service, try a few out, see if anything sticks. If not, you can email me and I can talk with you about my opinions about good vs bad services and if there isn't anything like it in the coding space, maybe you have your next start up idea. :-) Best of luck, whatever your future holds.

kohanz 12y ago

I've recently made a transition from full-time work to sparse, part-time freelancing, which I deem successful, but may not be by others' criteria. The parameters of my freelancing are undoubtedly much different from yours, but perhaps my experience is still of use. Up until May 2014, I was working FT at a small non-profit (government-supported) consulting firm in the medical devices space. At this point I had about a decade of progressive development experience and more than half of that in the medical space. I wasn't totally happy at that position for various reasons and, for some time, I had been interested in having more time to work on my own projects. Part-time work was what I thought I needed, but no employers were interested in that kind of arrangement. Also significant is that in April 2014, our first child was born and I knew that I wanted to be an involved parent. So as my son's due date came closer, I investigated freelancing as an option. Another factor that is important in my case is that due to my previous employment and my family's relatively frugal means of living, we are doing OK financially. We live in a medium-sized city in Canada where living costs are lower tha your bigger tech hubs. I knew that I could go a year or more with almost no income that we'd still be fine. I've come to realize that this is a blessing and a curse at the same time though ;) To be honest, some things just fell into place for me. One of the clients that I was the lead on at my day job was someone I knew that I could talk to openly and when I told them that I would be leaving, they showed immediate interest in retaining my services. My employer was fairly shocked at my leaving. I was (and I try to say this as modestly as possible) the most productive and reliable developer there and also the one trusted most with customer relationships. I gave them plenty of notice (6 weeks) and we left on very good terms. Here's the kicker, my old employer is now my #1 client. I am essentially a subcontractor to them. I make about 1.75x what I did as a FT'er on an hourly basis doing my old job for them, but I have the ability to set my hours, workload, and decide which projects I take on. It's almost funny to me because if they had offered me reduced hours and similarly reduced pay in the past, I probably would have taken it. I charge them a bit less than other clients, because they take the pain of finding new customers out of the equation for me. All this said, I bill about 50 hours a month. I could bill more (take on more work), but that isn't my objective. The other time I spend working on my startup and I spend an above average amount of time at home, being a dad. This is exactly the arrangement I was looking for and I couldn't be happier with life these days. This won't last forever. That's why I've got the startup in the works and also I know that, should I ever need, I have a reasonable number of contacts in my city to get another job (and I'm sure my old job would still be available should I choose to return).

larrykubin 12y ago

I successfully freelanced for years. I think one key for me was living in Austin, where there is no state income tax and the rent and food costs are low. It doesn't take many hours of consulting work to be able to live comfortably there.

MichaelCrawford 12y ago

This might help: http://www.warplife.com/jobs/computer/telecommute/ http://www.warplife.com/jobs/computer/telecommute/ I too am very skeptical of startups. I'd rather get paid by the hour, then get paid with a promise that's not likely ever to be kept. I understand one-half of American businesses - in general, not just startups - fail during the first five years.

mod 12y ago
Wouldn't these businesses all be startups? What is the differentiator in your mind?
- MichaelCrawford 12y ago
  Some are startups but most of the companies I list are not. I spent quite a lot of time puzzling over whether I should reject certain kinds of companies from my list. In the end I decided that I would not, but I do plan to make it more clear that the user is advised to research the companies before accepting an offer, or even before applying. To make that easier, in the future I plan to link to the Better Business Bureau, Glassdoor and the Securities and Exchange Commission pages for each individual company.