"I used to keep customers in my contacts and contact them once a month had passed to see if their interested again. I stopped doing that because I felt like 1. If they want my services they have my number and 2 I don’t want to seem like I’m asking them for money."
Lots of good advice here about acquiring new customers. I will comment on the gold mine you are sitting on - your previous customers. I started my small business 14 years ago. I am established, have a good reputation, and rely on repeat business. And if I waited for my customers to call me, my income would be cut in half. As discussed, people are lazy. They won't always contact me, even if they need something. So I contact them, then all they have to do is respond. I do some cold-calling by telephone, but that is inefficient. I work mostly by e-mail. I have an organized system where I contact every customer quarterly by e-mail. I have no qualms about asking customers for business.
Let's say you've worked for 300 different customers over the past few years. You organize their e-mail addresses and contact 25 per week. It will take you 12 weeks to get through them, then you start over. My guess is that you'd get at least one job out of every 25 e-mails you send out. It's an easy thing to do, you can do it at night while watching a movie or a ball game. And it's self-metering. Slow week? You have time to send out more e-mails. Busy week? Don't send out any e-mails.
Good luck, sounds like you're doing pretty well regardless.
