I’m No Longer Self-Employed (Life Update)

Yep, you read that right! I’m no longer self-employed.

I'm no longer self-employed

A few months ago, someone messaged me on LinkedIn and invited me to their studio for a TV interview. The studio was local to Jacksonville, and I was being invited to talk about my business, Imperfect Taylor LLC.

If you don’t know the full story, I was laid off last year while solo traveling in Paris, France (that was an interesting experience haha). I called David (my boyfriend) immediately after being laid off and one of the first things he said to me was, “maybe now’s the time to take Imperfect Taylor full-time”. I had been dreaming about the idea of taking Imperfect Taylor full-time for years at this point, and as soon as David made that comment, I made that my mission.

For the majority of 2023, I was working full-time on Imperfect Taylor. I was creating content, building up my blog (the website you’re on right now), holding coaching sessions, and building up my client base for both website clients and social media clients.


I almost gave up on self-employment

In full transparency, I almost gave up on self-employment at the beginning of the summer. I really thought about going back to the corporate world, and even started applying to a few jobs.

Things started getting really hard for me and I was very aware that my savings account was nowhere near the amount that it once was. Financial stress started kicking in… something I hadn’t felt since the beginning of my debt free journey in 2017.

That’s when someone I really admire put me in touch with a life coach. I’d never worked with a life coach before, but was willing to talk to anyone that could help me map out my next steps in life.

I knew I didn’t want to give up. But I was on a path that felt pretty lonely and a little bit scary. And I needed help.

Long story short, the life coach I met with was (and is) phenomenal. She helped my mindset around self-employment tremendously, and one of the best pieces of advice that she gave me was to start taking massive action. I needed to put myself out there more. And if I could do that, things would start to come my way.

And they did. It sounds so cheesy to say, but I truly believe in the law of attraction. And it was so obvious to me that once I started showing up in different ways (like, you might remember the webinar I did on overcoming self-doubt) that the universe or God (whatever you believe in) started to say… “OK Taylor, I see that you’re serious about this, so let’s do it”.

And soon after, things started picking up for me. Business began to steadily roll in. Opportunities started coming my way. I started thinking that maybe Imperfect Taylor LLC was a feasible business after all. Thank goodness.


My TV interview that changed everything

Shortly after, someone in the Jacksonville, Florida area (that’s where I live) reached out to me on LinkedIn to invite me on their TV show.

I wasn’t really sure what their company was all about, but after doing a little research, it was clear that they had interviewed a ton of business owners in the Jacksonville area. I figured it would be a free opportunity to put myself out there and maybe network with a few people, so I decided to do it.

On my interview day, I walked into the office, met a bunch of nice people, and had my interview. It lasted about 5 minutes, and I really enjoyed it. 

Here’s my interview if you want to check it out.

However, after my interview, I thought to myself… Why is this company inviting business owners in for interviews and offering them free press? There has to be something in it for them, right? What’s the business model here?

So I asked. And I learned that I was in the office of a full-service media company that hosts interviews so that they can learn more about business owners’ pain points and challenges so that they can ultimately offer them their services.

Whether that’s helping businesses with their social media content, building them a new website, helping them throw an event, helping them raise money for their nonprofit, etc.

And that made perfect sense to me. In fact, I thought it was pretty smart.

Before I left, the person who ran the place said they’d like to meet with me again soon. I wasn’t totally sure why but I figured it couldn’t hurt.

In the days before my next meeting with them, I started browsing their website for open positions. As someone who has always been interested in website design and development, I was immediately curious about a position that I saw on their website for exactly that.

At this point, I was still set on moving forward with my business. I wasn’t looking for a new job. But I figured I’d apply to the position just for kicks.

When I met with them again, we discussed the job I had applied for and we came to the conclusion that this might be a great fit for us both. That’s when I started thinking about how nice it would be to get a bi-weekly paycheck again (haha).


My new job

After a few more casual meetings and one “interview”, I was offered the web development job. I put the word interview in quotes because honestly, it never felt like an interview. I never felt like I needed to sell myself in any of the conversations that I had. And that was such a relief. And a sign to me that I might really be in the right place.

Everything came together pretty effortlessly and before I knew it, I was going into my first day at work.

I’ve gone from working for myself and working from home every day, to going into an office 5 days a week and working 9-5. You might think that sounds inconvenient. Shitty, even. But (thankfully) it’s quite the opposite.

I missed talking to people every day. I feel like this job gives me a sense of purpose that I didn’t really have when I was working for myself. I love that I am working toward a common goal with other people. And not to mention, I am learning so much every single day. 

I also have been appreciating getting ready for each day. Yes sometimes it feels like a hassle, for sure, but I feel so much better about myself when I put on a nice outfit, some makeup, and head out the door, versus staying in the clothes I slept in to work in my home office haha. 

My biggest takeaway though is that I am so much happier. I really thought that self-employment was going to be incredible in all of these ways, and while it had a few pros, it wasn’t what I hoped it would be. 

I think that’s partly because I didn’t really know what I was getting myself into, but also because my expectations for it were warped. I don’t want to say that I blame all of the people on social media whose marketing tactics involve telling you that if you buy their course, coaching sessions, etc. that you can become self-employed, make $10k a month, travel the world, work from anywhere, and ultimately have the best life EVER… but let’s just say they had me convinced haha.

I’m not saying that those things aren’t possible, but it just wasn’t the case for me at 8 months in. Entrepreneurship is tough. And I now have so much more respect for the people who grind it out and pull it off. One day I’ll have to write a post on expectations vs. reality when it comes to working for yourself.

I might try self-employment again in a few years, but for right now I feel that I am exactly where I am supposed to be.

I’m looking forward to sharing more of this journey with you. Please let me know if you have any questions or if I can share anything else! And if you’ve gotten this far, thank you so much for reading.





Other posts you might like:

32 Super Inspiring Career Advancement Quotes For Professionals

12 Incredibly Valuable Tips For Starting A New Job

7 Job Interview Preparation Tips To Land Your Dream Job



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About Taylor

A few years after graduating college, Taylor made it her mission to become debt free. After paying off all $60k of debt, she began to blog about what she's really passionate about: personal development. Nowadays, Taylor blogs about the topics of Mindset, Money, Health, and Career for women. Read more about Taylor here.

"It's Per$onal" is a super popular and anonymous blog series about the personal lives and finances of women all over the world. Check it out!

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