

Ask HN: Done with startups. Contemplating freelancing - consowels

(I&#x27;m a semi-regular HN participant using a burner login to hide my identity.)<p>I&#x27;ve spent all (15+ years) of my career at startups.  Several times I&#x27;ve been a single-digit employee and have unsuccessfully founded a company.  I&#x27;ve had one modest pay day but that money is long gone.<p>I think I&#x27;ve had enough.  I&#x27;ve grown tired of the ups&#x2F;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.<p>I&#x27;m exploring the world of freelancing.  I&#x27;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&#x2F;life balance.<p>Has anyone successfully made this kind of transition? Many thanks.
======
tptacek
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
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
> 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.

------
larrykubin
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
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
Wouldn't these businesses all be startups?

What is the differentiator in your mind?

~~~
MichaelCrawford
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.

------
kohanz
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).

~~~
consowels
Thanks for this. Becoming a parent is also part of my considerations.

~~~
cylinder
Look out for healthcare costs if your partner is not employed.

We don't really want my wife to work when we have kids; however, as a self-
employed person, the cost of purchasing you r own health insurance is
outrageous. For a family of two adults and two small children, it'll run me
over $12,000/yr and that's with a high deductible plan so there will still be
out of pocket costs.

Unfortunately, this sole fact is pushing me away from self-employment. That
people say the USA is friendly for entrepreneurs is absurd: perhaps if you're
well capitalized with other people's money, but not if you're doing
traditional self-employment / small business.

~~~
timjahn
Couldn't agree with you more on the healthcare costs. The difference between
being W2 employed with company provided healthcare for a family and being self
employed with self purchased healthcare for a family is absurdly huge.

America punishes those who don't work W2 through the healthcare costs and it's
just plain horrible.

