I'm not sure how much of this is aimed at OP and how much at me, but such things have never stopped me from posting before!
I've rarely done any side work because I have put in a lot of hours week to week directly employed in an enterprise environment, so I'm not too excited about doing any more when my workday ends.
I agree. In IT there is also on-call, off-hours maintenance, and often self-study, so 8-5 isn't 8-5.
Earlier in my career, working for a medium size IT VAR business, I provided network services to various smaller businesses in the area and sometimes to larger businesses as well. It was an established business before I ever worked there. I'm already FI, but I plan to FIRE in about 2 years, and I sometimes consider doing consulting or other IT services on a limited time basis, figuring that 30 years of full time IT experience should hold some value, but everyone who has learned some basics working on computers at home thinks they can start their own business, and by the time I differentiate myself and build up any client base, I will probably be wanting to throw in the towel to enjoy total FIRE. So, I'm thinking it might not even be worth the effort to ever get started, so I'm planning to work long enough here to build up a decent stache to provide a nice cushion over bare bones expenses. Once I exit the field to FIRE, I don't think re-entering will be that easy, especially at the level and salary I have achieved, which is all the more reason for me to stick it out now to build the stache (I hit 83% savings rate last year.)
I worked briefly for a startup in 2000 that catered to small businesses / home office. (
TechPlanet - I'm surprised there's still mention of them on the web at all.) Same tech concepts, just slightly different application. Like visiting another English-speaking country...same but different.
Working for a startup is not something I'd recommend, but on the other hand it was quite a learning experience. OP's mention of Chamber of Commerce events where everyone is selling and nobody is buying is very, very familiar to me!
Oh, and as a field tech for much of my early career I visited all shapes and sizes of businesses as on-site vendor support for one product or another they were using. I had never quite realized this angle of my experience before...I need to update my resume now!
But yeah, I've long toyed with the idea of working for myself, but I know it's not that simple. You have to find customers, bill them, follow up, file taxes...run a business. And I know that's not easy, and I know it's not in my core skill set. So yeah, working for "the man" has made a lot more sense.
People say to start on the side, but I'm starting to learn about myself is that I can only focus on one thing at a time (to a fault), so working for a company and trying to run a labor-requiring side business is just not going to happen for me.
So I was not looking to go into consulting. I think the turning point--aside from having at least a year's worth of expenses saved up, glowing references and relevant IT skills--was the out-of-nowhere thought that at this point in my savings and career, I could "drive for Uber for 5-10 years and still retire." But the point isn't Uber, and given my IT skills and my enjoyment of it it would be silly for me not to do IT. The point is I have the ability to coast to the finish line by earning enough to cover expenses and let my nest egg grow. So I have an opportunity to try something new and scary, and if I only half-succeed I am suddenly semi-retired.
But yeah, I would not have voluntarily left my job to try to start a consulting-business-without-a-plan, and the fallback position is to go running back to MegaCorps for a couple of paychecks a month and some golden handcuffs.
I guess I don't really have any specific advise and am posting more because it strikes closer to home for me. Was the full time job that you lost in IT also? And if not, have you looked into pursuing a new job in the field? I have had some friends that tried to make it on their own providing IT services, but they all ended up working for businesses/institutions.
For me, I am almost planning to fail. I have already forgiven myself if I fail to cover expenses and start running out of money within a year. And I'm not going to go looking for W2 work right away, but if my old company initiates contact or one of my ex-coworkers' new companies reaches out to me with a decent job offer, I'm almost certainly taking it. And yeah, my [ex-]job is in IT.
Getting customers should be the hardest part, but I may have identified a niche or two in which I may have half a foot in the door. I volunteer-migrated another finance forum...geez, 12 years ago now...and apparently that impressed quite a few people, some of whom later asked me to help with websites, but for various reasons--work--I either flaked out or outright said "nah". I've been running my own web servers for 12+ years at home without battery backup, so even in a case or two where I might have accepted work or volunteered work I steered them away because my home server could go offline for hours at a time, and they'd be better off someplace more consistent.
But cloud services and automation make it much easier for me to deploy reliable hosting, so I'm going to work on a service offering to start testing out in a couple of months.
But hearing that there are a bunch of law firms and small businesses needing desktop help...well hey, I can still do that and bring in some money!
