You're a mom. You can do anything. (yes, even manage your money)
Start today and download my FREE Mom's Got Money starter pack!
You’ll also get updates from me.

The Truth About Self Employment: My Transition

  January 15

This post may contain affiliate links.
The Truth About Self Employment
Me…Giving Blogging Two Thumbs Up This Morning

A lot of you have asked about my transition to self-employment, and I’ve been really excited to share all the deets with you!

I’ve been working 100% for myself for 15 whole days now, and it’s definitely been an interesting journey so far.

Like any other post, I’m going to be 100% honest and tell you the truth about self employment and what it feels like to completely break out on your own.

Of course, you have to take my personality into account with all this. Maybe some people can just quit their jobs and go about their self employment days free as a bird, but I tend to be a little intense so my story might look a little different than others.

Here’s how the transition started:

November 2013 – Feeling Incredibly Grateful

I got really lucky to have an amazing day job the past two years. I worked as a university instructor at my husband’s medical school, and I had two incredible bosses. When I found out I was pregnant with the twins and wanted to move back to the U.S. early, my bosses really, really supported me when I asked if I could work from home in November and December.

They agreed to let me finish out my contract from 3,000 miles away, which made me feel very, very grateful. Seriously, I won’t ever be able to repay them for their generosity and for trusting me to do my work remotely.

This arrangement gave me the opportunity to mix my day job and my online work. Like always, I was working a lot of hours every week between the two gigs, but without the structure of the 9-5 schedule, I was able to handle some blog stuff earlier in the day and then do my research for the university in the evenings when the Internet was quieter. This was a total flip flop from what I’d been doing the last year, which was doing my blog work at night.

So, this helped me to establish a schedule that carried over to now all while still getting paid my salary from the university.

December 2013 – Feeling Incredibly Excited

When I turned in my last project to the university, I felt really excited and accomplished. I was finally doing it – switching to self employment! I went to bed that night really, really happy, not because I didn’t like the day job I had, but because I was finally doing something that I’ve been working towards for a really, really long time.

Of course, everyone warns you that self employment isn’t for the faint of heart. It’s a very turbulent thing, and anything can break at any moment. Still, I had 6 months of very steady blog income with a big list of clients, and I knew I was ready!

January 2014 – Feeling Incredibly Terrified

On one of my very first days of self employment, I woke up to some bad news waiting in my inbox.

One of my regular clients decided to shut down their blog and said they would not need my writing services anymore. Then, right behind it, I had another e-mail about a dumb mistake I made on project from last year, and it cost me a pretty penny. It’s extremely rare that I have issues like this, but they all piled up on the same day and right at the beginning of this self-employment journey to boot.

Basically, after 6 months of awesome blog income, steady clients, and very positive feedback, I lost about $500 in one day. To make it worse, I was waiting on PayPal payments from about 4 people who were late, and so I basically spent the first few days of self-employment wondering if it was the worst idea in the history of ideas.

Getting the Support I Needed

I realized quickly that I couldn’t just sit at my desk and quietly freak out all on my own, but I couldn’t help but panic. As many of you know, my husband is a medical school student, and so for now, this blog that you are reading is providing the only income for my family.

I called my dad literally crying and basically saying, “Dad, I don’t know if I can do this! The pressure is unreal! Every single bill has to be paid from income from my blog! Every grocery purchase has to be made by my blog income! OMG I’m pregnant with twins. My family is going to starve.”

Obviously, my mind was seriously wandering. I was legitimately wondering how I was going to pay for my health insurance or my moving costs or be able to find a nice home or decent home insurance one day if I was the sole provider.

My dad was just like, “Catherine, if you keep thinking things like that, you’re going to cause yourself to jump off a bridge. You’re not going to starve. Just take one thing at a time.”

Of course, the hubs was extra supportive too. He was all, “We have tons of savings. You have had a steady income for 6 months. You can do it! We will be fine!”

From Paralysis to Punching Fear in the Face

Honestly, I was really surprised at how quickly the fear set in. I thought that I would feel super confident and ready to go in terms of self employment since all the numbers pointed to success. But, when everything wasn’t going perfectly those first few days, my mind really started to wander.

I even spent a whole day last week unable to do any work at all. It was like I was completely paralyzed.

I e-mailed my friend John, who many of you know, and I was like, “I’m paralyzed with fear! What do I do?” His suggestion was to take the fear and turn it on it’s side and use it to kick some ass. I might be paraphrasing a bit. But, his suggestion gave me a little bit of a pick me up, a sense of power, a knowing that of course I can do this. It’s my business! I made it! I can make it work!

Things Are Great Now

A few days ago, I finally got a few payments I was waiting on. I set up some advertising for January. I got an e-mail from someone new who was looking for a writer. A friend asked me to guest post on their blog. Then, I got an e-mail from someone who asked me to be their mentor and help them become a freelance writer. That made me realize that I do have some valuable knowledge and skills and that I really can do this. In fact, I’ve been doing this for months now. Self employment has just given me the time to do an even better job at it.

I want everyone who is interested in doing the same thing to know that I didn’t pick self employment lightly. I had good work ethic, a lot of savings, and an idea of how to move forward. I am a planner, and I would never risk the well being of my family if I didn’t think it would work.

Yeah, as evidenced by this post, it’s scary, and yeah I had a rough start earlier this month, but what a difference a few days can make! I always tell people that’s the fun thing about blogging – you never know who you’ll meet and you never know what fun projects will come your way.

You also don’t know when your server will crash etc. but every business has bad days. It’s just a matter of having the experience and the willingness to push through it to get to the good stuff. At least, that’s what I’ve realized in my 15 days of self employment wisdom. πŸ™‚

So, all in all, I still feel like I made the right decision, and I’m working on just taking things day by day and jumping over the hurdles as they come. I really appreciate all of you following along on the journey, and I’ll definitely keep you updated as things happen along the way!

Is anyone else thinking of making the switch? Spill it!

39 responses to “The Truth About Self Employment: My Transition

  1. Thanks for this insight, Cat. It’s great to hear a candid look at the realities of freelancing, and that really comes through in your writing.

  2. LOVE the paraphrase Cat! You put it much more succinctly than I did. πŸ™‚ It happens to the best of us and you’re right on – those bad days do happen and we have to push through them to get to the other end. I hate that fear, but what I’ve found is that it really teaches me a lot about myself and can be a great motivator. Keep up the awesome work Cat, you’re doing great!

  3. We’re not thinking about self employment anytime soon, but it’s great that you’ve been able to fulfill this dream. Wishing the best for you!

  4. Oh yeah, I love these types of “real life” posts about self-employment. It’s not always an easy thing to run your own business and be the sole provider of your household (I can totally relate). But I’m still thankful I get to wake up everyday doing what I love and get to interact with amazing solopreneurs like yourself. You have great things ahead of you!

  5. Thank you for sharing the ups and the downs. I feel like I’m on a hamster wheel recently, spinning and spinning and going nowhere, but hard work pays off eventually. It just takes an email in the inbox to turn a day around πŸ™‚ Glad yours did!

  6. Thanks for sharing your experience Cat! Know that you are not alone! There is a great scene from the movie Tangled where Rapunzel leaves her tower for the first time and she switches from elation to utter fear within seconds multiple times. I tell people that is what having your own business feels like. Keep up the great work!

  7. I love the description of the phone call! Seems like I heard about something similar at the start of the thesis? Keep posting; I always enjoy your reflections.

  8. Congrats on taking your first few steps into self employment Cat! This is a huge adventure for you and from the last 6 months it looks like you’ve already proved that you can do it!

  9. Thanks for sharing about your first couple of weeks. I figure it would be pretty daunting cutting all the safety ties at first to go out on your own. It’s great that you’ve got that support and have planned for the downsides. Just remember to celebrate the upsides too. Love your work!

  10. Ah sorry to hear about one of your client’s shutting down their blog. I’m surprised they didn’t sell it. To be honest, having some of the writing outsourced could only make it more attractive to a potential buyer (imo). Anyway, that’s enough thinking out loud πŸ˜‰ It’s really awesome that you are working for yourself and I can’t imagine the pressure you are under. You are a hard worker and seem to have built a solid foundation of clients and I think opportunities will keep coming your way for more work.

  11. Congratulations Catherine! On your beautiful babies to come and your recent move to self-employment. You are an inspiration. I hope to be where you are in my future. Hang in there, you are doing amazing things. πŸ™‚

  12. Thanks for the insight. I’d really like to become a freelance writer and I have a lot to learn. It sucks that sometimes things go wrong in one day, at the beginning and it makes you doubt yourself. Life throws you tests sometimes to see if you are serious, you know? I just tell myself that, “ok this is a test. don’t give up now.” I am also the breadwinner in my relationship and while my partner helps close to half, his income is very volatile and feast or famine. I want us both to grow into entrepreneurs and be successful. You will do great and as time goes on it will get easier.

  13. So glad to read such an honest view of self-employment! My “holy crap I’m going to die penniless in a ditch” moment didn’t come until I was about 2 months in, and I have them regularly even after 2 years. Don’t give up – the internet is wide open and if I can do it, anyone can! You have too much talent to waste it working for someone else. πŸ™‚

  14. I am sorry to hear that things went bad before they got better… but at least they got better. It was really unfortunate to get punched twice in the same day and I completely understand your fear – I guess that anybody in your situation would’ve reacted the same. But, just like you did, you just have to step up your game, understand that things won’t be bad forever and do something to change them. Glad that you’re now back on track and I am sure that you’ll do better than ever!

  15. Hi! My name is Elloree and I really enjoyed this post. My boyfriend of 5 years just moved to Grenada a week ago to start the charter program that will hopefully have him in medical school at SGU in August. We’ve been discussing my moving with him after my graduation, but the loss of my income will be financially painful. So, lately I’ve looked in to freelance work and have been really inspired by the journey you took making your Grenada transition. Living without him for two years would be just too difficult and your advice has definitely helped me find the confidence to pursue self-employment options and given me insight into being with someone in medical school, so I want to say thank you so much! This blog has been immensely helpful, and congratulations on your career and growing family! πŸ™‚

  16. Congrats on going self-employed, I’m sure you’ll do awesome πŸ™‚
    I’ve been self employed for a year now, and what I struggle with is finding a balance between work time/home time. I usually start working around 10am, and go up until 10pm~12am, then go right to bed. Sometimes I go crazy from just staying in my condo all day, everyday, working and living in the same space.
    How do you organize your day? Do you stay at home to work all the time, or do you ever go to coffee shops to work, etc?
    How do you stay on track with working on just work stuff, and not veering off and checking on the laundry or doing dishes? Do you mix the two, or keep them seperate? πŸ™‚

    1. Ooh I am doing about the same as you – starting late and staying up super late to finish things! I am trying to get better with a schedule. Generally I do stay at home and don’t go to coffee shops, but I’m a super introvert and don’t need to get out the house that much haha.

  17. Thanks for sharing this as a realistic look at the beginning of self-employment! I know that it probably will be ups and downs but it seems like you should be pretty stable and successful overall considering your blog income is steady and you have a lot of clients. When one vanishes another comes along!

Comments are closed.
Copyright Β© Catherine Alford.  Designed & Developed with by