I got my start with Linux in 1995, and knew right away I wanted to
somehow make a career out of it. I loved trying to figure things
out, and Linux of that time period delivered. Slackware, Red Hat,
and Debian were the main ones I tinkered with, all rough around the
edges and generally requiring _days_ to get fully setup with X
windows and dialup internet.

I started consulting a few years later. A friend of mine was
starting a company, and needed someone to setup some servers (print,
file, web) and internet access. He had very little funding and just
a few employees - a perfect situation for me to evangelize Linux.

I setup a small network of Red Hat 5.2 servers (I still have the CD
set) on old hardware, mainly desktop PCs that were being
re-purposed. Internet access was dialup. I had one server setup as a
firewall/router that would activate its PPP connection on demand.
Needless to say, the employees had to do most of their work offline
and connect only when necessary. That setup lasted a year or so, but
they grew out of it quickly.

What is interesting about that time period - late 90's to early 00's
- was that much of the knowledge needed to do this was in
books. Google search had just come into being, and while it was far
better than the alternatives of the time, the web was still in its
infancy (the running joke nowadays is that a sysadmin's job is
mainly searching for answers on stack exchange). So I learned how to
setup firewalls and networks on Linux from a book, and lots of trial
and error.

When my friend's company finally upgraded to a T1, I moved the Linux
firewall/router to a real server, and switched to Debian (which
became my favorite general-purpose server distro for many
years). Later I migrated the single box to a failover pair of
OpenBSD firewalls running CARP.

Meanwhile I was doing other work as well - I had started full-time
as a security engineer at a small company providing managed security
services. I kept on doing side consulting for my friend's company,
and got involved in the local Linux user group scene giving
presentations. That led to more connections and consulting
opportunities.

Convinced I could make a living on my own, I left my full-time day
job in 2005 and started full-time consulting. This lasted about
seven years and was a mish-mash of system administration,
programming, technical writing and training. You can see some of my
blog posts from this time period, I've converted them to text format
and placed them here [0]. Eventually I settled down and went back to
full-time employment, mainly because our young family at the time
needed income stability, or at least I felt it did.

I do miss being my own boss, although at this point in my IT career
I don't think I'll ever go back. I still enjoy tinkering, although
it's not the same. The Linux ecosystem is so much more complex than
it once was, and generally things are done for you now. I'm not sure
that combination is a good thing if you're young and want a career
as a sysadmin or in network security, it seems like nowadays one
mostly learns how to use closed-source apps or some $BIGCO's SaaS -
the inner workings of it all are hidden beneath layers of
abstraction or are even inaccessible. Fine when it works - not so
fine when it breaks.

[0]: gopher://gopher.unixlore.net/1/articles/historical-blog-posts