08.08.12 Career & Finances

Dark Side of a Dream

Dark Side of a Dream


You’ve all heard the stories. You know the ones where the 30, 40, or 50-something woman gave up the high-powered, stress-filled 9 to 5 life and started their own business selling homemade, organic (insert product here), made a fortune doing it and now gets to spend quality time with her (insert number here) children.

But what about the ones who have tried and failed? Or who are struggling to see the dream of working for themselves pay off? You don’t hear about those stories, or read about it in women’s magazines. You only hear about the ultra-successful ones. But I can tell you there are probably more of us out there who struggle. Who really want that dream to happen, but find they are lost or swimming upstream.

I’m one of them.

Although I was not in a high-powered job and don’t have any children, I did have a nice, comfy job in corporate America as a video editor, which afforded me fun, leisurely activities, vacation time, health benefits and a 401(k). I was 38 and had a long-term boyfriend I thought I’d spend the rest of my life with, as well.

First, the boyfriend broke up with me. Then I was laid off from my job of eight years, right at the height of the recession in 2008. Although the idea of working for myself never occurred to me before, what better time than the present? And truth be told, I was feeling a little burned out from the daily grind. Having known and worked with video freelancers throughout my career, it didn’t seem like a bad direction to head. In fact, I actually turned down a full-time job offer, because I didn’t think their corporate culture was a fit for me.

Right off that bat, I had a project with a big, fat budget and life was good. I was also getting six months severance on top of any freelance work, so I built a nice emergency fund for myself and thought I would just breeze through this freelance stuff, no problem. But the jobs stopped coming in. The severance ran out. And I was spending money as if I still had that full-time cushy job, and not coming up with any solid plan of how to brand myself, find jobs or plan for my future.  I never even had a budget!

In the middle of all this, I decided to pursue another passion and enroll in classes to become a certified life coach. Never mind the fact that not only was I spending more than I was making, but I had in no way come up with a solid plan on how to fund this potentially new career, so I financed my education on plastic. After taking a couple of courses, I realized just how overwhelmed I was.

Here I was trying to find time to run one freelance business, taking life coaching classes and trying to come up with the time and resources to start yet another home-based business, all without making enough money to fully support myself. Finally this year, after three years of freelancing, I hit my rock bottom.

I realized that I was going through life on a wing and a prayer. I’m all about hope and faith that the Universe (or whatever your belief system is) will take care of you, but let’s be realistic, shall we? The Universe isn’t going to send me magic checks in the mail while I’m off having dinners out, using my $110/month gym and taking private beach volleyball lessons. Reality hit me hard, and just in time, as my emergency savings had whittled down to next to nothing and I still had no idea how much money was coming in or out.

Having a massive financial hangover, it was time to come up with a plan, and it began with the simple idea of having a budget  and knowing how – and more importantly, why – I was spending my money. I also decided that trying to run two home-based businesses was too much at one time, and put life coaching on hold in order to focus on securing myself financially before giving it another try.

Now, I don’t want people to assume that just coming up with a budget is the be-all, end-all solution to their financial situation, because it isn’t. That’s just the first step in a nice long journey to taking control of your finances. But I can tell you this: any time you start to gain control of your life in any area (weight, money, relationships, etc.), you start to feel a sense of relief.

It hasn’t been an easy journey, and there have been many challenges and setbacks along the way (last month I had to spend $2500 out of pocket on dental work), but at least I have more awareness about my money, and spend more mindfully. So if you’re in a situation where you are ready to begin working for yourself, or you end up there by accident, please take my advice and really sit down and come up with a plan and set goals.
Know where you are right now, and get information about what obstacles you may face in your journey. There are also many personal finance books and blogs that are full of useful information to get you started.

If you are a freelancer or self-employed, what challenges have you faced in your journey?

T.L. is a freelance video editor & blogger living in Los Angeles. She enjoys movies, running, and playing beach volleyball. You can follow her personal finance journey on her blog at Budget & the Beach, and follow her on twitter at @beachbudget.


  • For those wanting some more freelancing tips, I wrote a guest blog called On My Own which highlights some of the things I’ve learned along the way as a freelancer. http://www.debtandthegirl.com/2012/08/on-my-own.html

  • CJefferson

    Thanks for keeping it real! I’m one of those people who needs financial security (although you can never be ‘secure’) and have trouble with the idea of free-lancing working for me…but the major pay-off seems to be having some control over your own time. Either way your message is clear, do what works for you, but be prepared. Thank you for sharing.

  • Brigitte

    Great piece Great perspective.

    I have a similar story – including the 2008 timeframe as well as hitting the ground running as an entrepreneur with some great paying clients and project. I thought the same thing you did… I would say to myself.. “This is only the beginning… this was a lot easier than I ever dreamed it would be and the money is great!!! Wheeeee!” Then all of the sudden…POOF! by the summer of 2009… everything came to a stand still… Clients didn’t pay their retainers or balances due and I… I’ve been on this financial free fall since…

    I don’t believe that most people realize how challenging it can be to be an entrepreneur or freelancer. It’s like riding a roller coaster and if you don’t have the emotional stability to handle those ups and downs.. you can spend many of your days not wanting to get out of bed and wondering how you’re going to feed yourself.

    But… the bottom line is nobody would probably listen to us anyway and they’ll have to learn for themselves about rollercoaster called entrepreneurship… although I don’t regret what I’ve done or experienced being an entrepreneur… and I’m grateful for all I’ve experienced and learned, there is a lot of pain and uncertainity in taking this path… and the trade-offs can often be unbearable.

  • tam

    Great article and info, thanks. I can relate to all of it. I always felt the only way to not be on that roller coaster is to be financially ready for the slow times. Not that I am, but I’m working towards it. If you think about it, every business, pretty much without exception, has down time. But I know for me, at least, it’s taken alot of self-examination, and growth around finances and not relying on others to take care of everything. I have to work hard at this everyday. It’s really a challenge especially in these times, but when it goes good, it’s great.

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