Conversations with Myself, Part 5
A Conversation With my 40 year-old Self

In the last (so far) of these conversations, I had just turned 40. This is set a few days after my 40th birthday in 2014.
Me: How’s it going? Happy belated birthday by the way!
40 year old me: Thanks! It’s actually going pretty well, I accomplished a major goal that I set for myself!
Me: Oh really? What’s that?
40 year old me: I published my first eBook.
Me: Way to go! What’s it about?
40 year old me: It’s about some of the different companies that people can work for from home, and it also provides advice about some of the different things that people will need to consider when they start working from home, like paying self-employment taxes and how to balance their work with their home life, things like that.
Me: Sounds really interesting, what made you decide to write it?
40 year old me: Well Kevin bought me my first Kindle a few years ago for Christmas, and I started reading eBooks on it and saw that a lot of them were really poorly formatted and had spelling and grammar errors — I kept thinking “I could write a better eBook than this.” So I downloaded an eBook about how to write an eBook and sell it on Amazon, and I made it my goal to publish my first eBook by the time I was 40.
Me: And you did it, that’s great! How’s it been selling?
40 year old me: Not too good, I don’t have a lot of money to spend on marketing, so I haven’t been able to promote it as much as I would like to. I’ve been working on it though.
Me: Well that’s great, that’s all that matters. And its great to see that you’re still working from home.
40 year old me: Yeah it’s been 11 years now, I can’t believe it.
Me: Where you working now?
40 year old me: I’m working for a company called Apptical.
Me: What do you do?
40 year old me: I take calls from insurance agents who want to sign their applicants up for life and health insurance. Then in most cases I run the application and let the agent know based on what I get back of the applicant is eligible or not, and what level of insurance they’re eligible for.
Me: Sounds great! How long have you been working there?
40 year old me: Since 2011.
Me: Great! What else have you done since I talked to you last?
40 year old me: Well after I lost my contract with West Telemarketing, that company I had gotten a job with in 2003, I got a job with a company called Onsite — instead of taking calls I was doing what basically amounted to data entry work. Problem with that job was that the work was project-based, and there weren’t always projects available, so the work was sporadic. I did find some other jobs though, I did phone work for a few different types of companies, and then in 2011 I got the job with Apptical. I like it because I’m working as an employee so my taxes are taken care of. At one point I actually owed a few thousand dollars to the IRS — it took me several years to get that paid off.
Me: That sucks. It was good that you got it paid off though.
40 year old me: Yeah but I hate having to stick to a schedule. I want to get back to working as an independent contractor.
Me: Well when and if you do, make sure you set aside money to pay your taxes.
40 year old me: Oh I will, don’t worry.