Have you ever flushed $6,000 down the toilet? (and Other Business Mistakes)

In April, I celebrated my “self-employment anniversary” – I’ve been working for myself for over two years!  The first year was filled with so many learning curves and opportunities for growth I documented it ad nauseum (much in the way someone documents their engagement or new baby.) Here’s what I’ve covered so far:



So, What to Say About Year Two?

I've said plenty, apparently.


Despite the negativity and soul searching those posts (you guys know I often write to process), this year was immensely easier than year one in a lot of ways. After two years I finally have begun to feel like “working from home” is my new normal although it took me much longer to get to that place than I expected. For those who just took the leap and are working from home and feel super weird about it, in my own experience it took me nearly 18 months to feel comfortable working remotely. I was also

I was also constantly reinventing my schedule and routine trying to find the magical, elusive “way I work best.” However, with this newfound comfort, I felt enabled to take a lot of big risks and make some very large (and expensive) mistakes.

So, I thought instead of detailing every mind-blowing thing I learned in two years, I’d instead detail my biggest mistakes and embarrassments and perhaps my dear readers might be able to get something out of it.

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Mistake #1 – Not Giving Myself Enough Financial Runway


This isn’t a mistake I made in my second year, but it's my very, very first big “business” mistake that I’ve been reaping the seeds of since I left my full-time job nearly two years ago.

I can’t tell you exactly how much you should save before leaving your full-time job (and even this Quora thread doesn't have a definitive answer), but I recommend saving as much as you can before taking the leap.

Instead … I paid off my debt, saved up 3 months worth of expenses, peaced out and, honestly, I truly wish I’d done it differently. In thinking on it, I would’ve stayed at my full-time job probably another six months to give myself even more cushion.
Related: How to Balance Your Side Hustle on Top of Your Full Time Job


Mistake #2 – A Pricey Re-Brand (That I Immediately Trashed 90 days later)

I’d been feeling like I wanted to rebrand my former site, L Bee and the Money Tree, for a good two years before I did it. So, when I finally felt brave enough to let that brand go, I wanted the new site to be THE BEST THING IN THE ENTIRE WORLD, and I didn’t care if I had to pay through the butt to get it.

I found a development company who did the site for a big-name fashion blogger I really loved and they agreed to work on my site.

The only problem was the finished product didn’t work very well and the new design had some glaring UX flaws that both I…and the company I paid to “rebrand me” didn’t pay attention to. Finally, after getting so fed up with frustrated emails, lagging affiliate click thru and email sign ups, I bought a $59 theme off Etsy and installed it myself, basically throwing my $6,000 rebrand “investment” down the toilet.

I’ve always been a fan of designing my own sites (I like getting my fingers dirty and knowing how everything works.) I’ve never… ever been 100% happy with a site someone else designed for me and I don’t know why I let the idea of this big “rebrand” shake my money values so much. I guess I was feeling very insecure about my business and wanted to spend to make up for it. Which, actually, is a lot like shopping addiction. 

Mistake #3 – Not Asking Enough Questions


Similar to my home renovation, I didn’t ask enough questions during my rebrand. I’ve always been bad about (naively) assuming everyone you pay to do a job just does their best work without any extra push or questions asked because that’s how people are supposed to do business. 

Unfortunately, I've learned that some people don’t always do their best work or have your best interests in mind when they take money from you.

Questions like: “What exactly is included, ” and “What if I am unhappy with your work?” or “What if I need to make changes.”

My new policy: No matter what it is, or who I’m working with – if there’s some type of financial transaction going on – I ask a question. Even if it’s a “dumb” question or one I already know the answer to.

Here’s why: Asking a question (any question) shows that you’re paying attention… that you’re the type of person who is going to ask questions should an issue occur. This lets people know the type of person they’re going to be dealing with throughout the transaction is attentive and alert. You’re a question-asker, dangit! 


Mistake #4 – Making Purchases without Thinking Long-Term ROI


The re-brand was expensive, but I also wrote off over $30,000 of expenses last year because I’m the type of person who is always looking for the new and improved thing (especially when it comes to my business.) I'll ask myself, “Is this the app/the design/the plugin that will catapult my blog earnings into the heavens?”


But over the last two years I've learned that while it’s okay to invest in your business, it needs to be done strategically, and with the end result in mind. Instead of asking “what will this do for my business?” be extra specific and ask, “Am I going to get (x amount) of value out of this expenditure?”



Mistake #5 – Allowing the Emotional to Affect the Creative

It was (slightly) more acceptable to get caught up in daily drama when I worked full-time, because if I had an off day/week/month – I still got paid so long as I showed up. When you work for yourself, particularly when you own a “personality brand” that is tied to your own emotional wellbeing – things can spiral downward quickly, well, when the person behind that brand feels like shit from all the emotional turmoil at home.

I’ve written about this at length in this post, but my biggest point is that if you’re working for yourself you have to protect your emotional bandwidth with everything you have. I've even learned in the last few months that physical and emotional well-being are probably more indicative of success as a solopreneur than anything else.


These are just the highlights from year two. What's one of the biggest lessons you've learned being your own boss? I'd love to hear it in the comments!

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  • Michelle
    May 2, 2017 at 8:02 am

    I love that you’re willing to share your business mistakes. It’s uber-helpful for us new entrepreneurs! I can so relate to your problem with “assuming everyone you pay to do a job just does their best work without any extra push or questions asked because that’s how people are supposed to do business.” I’m sure you’re getting a whole new round of that with home improvement contractors 😐 Looking forward to following you and reading all about your future mistakes 😉

    • Lauren Bowling
      May 2, 2017 at 8:30 am

      Sometimes it feels like the only thing I have to share ARE the mistakes and the lessons, but I’m glad someone is getting something out of it 🙂 Thanks for stopping by!

  • Money Beagle
    April 26, 2017 at 2:03 pm

    I do some of my catching up during my lunch or down time at work and your ‘rebrand’ site had something in it that was blocked by our firewalls. Now it seems I can read it again. So, there’s another benefit.

    You live and learn I guess.

    • Lauren Bowling
      April 28, 2017 at 9:13 am

      I remember you mentioning that back when it happened. Glad it’s all fixed now! Yes, my old site was junk 🙁

  • Amanda @ My Life, I Guess
    April 24, 2017 at 1:30 pm

    I’m not exactly my own boss to the extent that you are, but I have been trying to run my website more like a business, lately. And you’re not kidding, there is a lot to learn! I work best when I have a routine, but I haven’t been able to get back into one for years now, and I know that that is leading me to make my own mistakes. But I think the biggest lesson I learned is a lot like you’re #5. You can’t run a creative business if you’re not well yourself. Your well-being needs to come first, no matter what.

  • giulia
    April 24, 2017 at 12:16 pm

    Love this kind of post so I know that I’m not the only one that make mistakes into financial world, also if I’m debt free into finance, oney & budget I am a constant work in progress:D

    • Lauren Bowling
      April 25, 2017 at 12:58 pm

      Everyone is a work in progress – it’s one of our five core money beliefs!

  • Colin @ rebelwithaplan
    April 24, 2017 at 12:44 am

    I always love when you write these posts! I really love the layout of how your site is now. It’s easy to get to the different sorts of content.

    • Lauren Bowling
      April 25, 2017 at 12:59 pm

      Thank you! That means so much coming from you, Colin 🙂