Here's what I tell others in my industry - design - which may be related.
In general, age never matters to any real degree. Most of my clients have no clue how old I may be - and they don't care.
Experience matters. The more years of experience you have the better off you are in terms of marketing yourself. However, high-end, visible experience will outweigh years of non-visible experience (example: developed some well known iOS apps but only have 3 years experience as opposed to 10 years experience working for "johns programming" where nothing is publicly known).
I don't know your market, but in mine.. Craigslist is about as far away as you can get from finding good clients. You need to network and find clients via word of mouth or referrals. Join the Chamber of Commerce, seek local social groups dedicated to your field. Tell people you know (not other employees) that you want to start finding jobs you can complete in your spare time. Look at the dedicated employment web sites - NOT craigslist. The employment sites (in my experience) aren't great for maintaining a freelance career (in my field) - they make you work way too hard and rarely have repeat clients for you - but they are a way to get your foot in the door.
My general seven steps to preparing to freelance full time
- First, figure out your rates. Know the minimum you need to charge if
you were working freelance. Once you know the minimum, add 20-50% to
it. This will provide some profit margin. I won't go into
calculating your rates, but there is an excellent answer over at
GraphicDesign.StackExchange.com regarding this. It would apply
to any freelancer.
- Second, figure out what unique tools, skills, knowledge you
bring to clients as opposed to your competition. Look at your skill
set from an outside perspective and be honest with yourself
regarding your skills. Are you exceptionally skilled in a specific
area? Are you grossly under skilled in a commonly needed area? Think
about an "elevator pitch" for clients - a short 30 second to 1
minute paragraph which defines why you would be valuable to them
were they to work with you. You should be able to recite this off
the top of your head - not in an "I practiced this" manner, but you
should be able to clearly explain your value.
- Third, use the above two items and work in your spare time. Dedicate
a couple hours in the evening each day and time on the weekends to
work freelance projects. This will build a stable of clients
while you still have the security of employment. This will help you
learn the ins and outs of client-based work. It's much different
than being employed. You need to be far more diplomatic, less
willing to complain, and always willing to smile. It also takes
practice to learn to say "NO" to a someone willing to pay you. This
"spare time" work will be invaluable in learning how to deal with
clients and the job you have will provide a safety net while you
stumble through it at first - like we all have.
- Fourth, while working this part time freelancing, pass on the
smaller inconsequential projects. Remember, you're looking to build
relationships with high-end, repeat client. You don't want to waste
time on the small one-off, no repeat, down-and-dirty, projects. You
want clients that appreciate and respect your work. Don't bid/quote
on anything which is not "shooting for the stars" for you. Go after
those high-end projects. After all, if you don't get them you still
have your job and that paycheck. So, aim high.
- Fifth, save money. While enjoying the regular paycheck tuck part
of it away. As much as you can. Before even considering
freelancing full time you need to have a minimum of 6 months to
live off of. More is always better. If you have a family or large
debts, you may want to consider a minimum of one year salary before
considering full time freelancing. Remember to factor in things your
employer is currently paying for - healthcare, 401k, dentists, etc.
These expenses will be yours if you are self-employed. Figure out
your "cushion" - that is how long you could go without any income
and still be okay. If it's under 6 months (or preferably a year) you
aren't ready financially to make the move to full time freelancing.
- Sixth, pay down debts. Try to eliminate any ongoing debts you
may have. Pay down credit cards, get rid of store credit cards, pay
off a debt such as a car if possible. Basically, you want to get
your monthly debt to income ratio down to as little as possible. The
goal is to have as much money coming in as possible while needing
to pay out the smallest possible amount each month.
Repeat all the above regularly. Keep working towards these six items until you think you have them down solid.
- -Evaluate- Evaluate yourself honestly every couple months. And I do mean honestly.
- Are you maintaining the part-time freelance clients?
- Are you always looking for work?
- Are you struggling financially?
- Are you missing freelance deadlines?
- Are you finding your freelance clients are often upset or dissatisfied?
- Are you turning away projects due to your own lack of knowledge/experience?
- Are you not following through with freelance opportunities when the present themselves?
answer to any of this is "yes" you aren't ready and you need to
focus on the areas you aren't meeting. These are very important
when freelancing. You need to be dependable in addition to having a
dependable income stream.
When to jump.....
When you have a stable of repeat clients that keep you working most of the time (during your designated freelance hours) without any great need to go find new projects, you have that 6 months/1 year of saved income, aren't currently struggling to make financial ends meet, and you are bringing in enough freelance money to sustain 3/4 of your debt each month.... you are probably ready to make the leap to full time freelancing.
In my experience, having a stable of good clients, even if they are merely part-time clients before you quit regular employment is critical. Don't even consider freelancing full time if you have no repeat freelance clients.
Then of course there is option 2.....
Just quit and start doing it. Be prepared to bomb and need to frantically find a new employment position if things fail. And be prepared to struggle if you can't find that new employment. Some people thrive in chaos and it motivates them. I would not recommend this method, but to each his own.
In either situation there is risk. If you are the type of person who is risk-adverse then you need to ensure the seven steps above are taken care of completely. Yes it can be scary.
After you make the leap... give it 90 days. If after 90 days of full-time freelancing you aren't facing any any major concerns in terms of finances or workload, you'll most likely be fine and things will only improve. If after 90 days you aren't bring in enough money or aren't finding any work then you may want to start looking for other employment. However, thanks to the cushion in #5 above, it won't be a frantic rush to "save the house".
Remember to always keep that "cushion". Freelance income is feast or famine - you may do great one month then not so great the next. So, during good months don't go rushing out to buy new equipment or something. Remember lean times will come so be prepared for them.