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My Boss is the Coolest!


Today is my first official day of being self-employed. Like the awesome boss that I am, I gave myself last Thursday and Friday off to get organized and prepare to work harder than I’ve ever worked in my life.

Other than my parents, very few people know that I’ve made the jump to working for myself. I didn’t want to stress out the rest of my family right before Christmas, and since they expected me to have two weeks off at Christmas anyway, I see no need to tell them just yet. I’d much rather wait until I know how things are going to go and what I’m doing.

I did tell one friend, who had a complete meltdown. He is very much entrenched in an employee mindset, and he just can’t fathom the idea of taking a risk. “I could get you a job where I work!” he said. “You’ll have benefits and guaranteed income, and you can continue writing on the side.” Um, dude, that’s exactly what I DON’T want to do. Because I’ve learned that working for someone else is no guarantee of income OR stability.Β 

So how is this going to work?

A lot of you have asked me what I plan to do and how I’ll survive without a paycheck. (Not that my paychecks were helping me much, anyway.) So here’s the plan as of right now:

Making money: I have started another site, not finance-related, that should bring in quite a bit of income from search traffic. I’m not quite ready to reveal details yet, but you guys will be the first to know once it officially launches. I’ll also be writing some slightly more serious posts here that should please the Google gods and bring more traffic. (Never fear – I promise to balance the boring stuff with interesting posts!)

This site already brings in anywhere from $600-$800 a month with little effort, so if I can double that between both sites by April, I’ll be in pretty good shape. I’ll also be doing some freelance/staff writing to bring in extra money. I haven’t ruled out the possibility of a part-time job, depending on how the first few months of the year go.

My budget: Now that I don’t have commuting and other work-related expenses, my budget is a lot more flexible than it was before. I also deferred my student loans for another year to give me time to get a routine going. These are the expenses I have now without cutting anything:

  • Fixed expenses (car payment, car insurance, phone, internet, utilities): $650
  • Gas: $75 (I’m assuming 2 tanks a month since I get over 40mpg and won’t be going anywhere most of the time)
  • Food: $300 (guesstimate)
  • Cigarettes: $110 (I know, I know)
  • TOTAL: $1135

That’s as barebones as it gets – obviously I’ll have other expenses, but I’m trying to figure out the minimum I’ll need to survive. I honestly don’t think it will be too difficult to meet that number every month, but I also need to keep in mind that I’ll be withholding my own taxes. Probably not during the first month or two, because I need some time to figure things out, but then I’ll have to make up for it later.

What will I be doing all day?

I know myself well enough to know that I need a schedule. Otherwise it’ll be noon and I’ll be on Twitter talking about movies or boobs or something.

My days will start at 7 AM with email and random online stuff before I get Jay up for school. After I drop him off, I’ll be writing from around 8:30 to 3 (with more email and such sprinkled in). From 3-7, I’ll be picking Jay up from school, making dinner (I have a goal to actually eat real food now that I’m home), cleaning, helping with homework, etc. Then I’ll hit the interwebs again from 7 to around midnight while Jay is playing the Xbox and going to bed.

This actually isn’t all that different from what I’ve been doing, except I don’t have to wasteΒ spend time going to work when I could be writing. I probably won’t have as much to do at night because I’ll get it done during the day. And I have enough discipline to actually do this stuff – it’s different when I have to do it to pay my bills.

Some Random Inspiration

I’m a huge fan of quotes – not those sappy “dance in the rain” quotes, but ones that actually inspire me to keep the faith and stay motivated. I’m in the process of making an infographic of sorts from some of my favorites, which I’ll frame and hang up in my home office. Here is one I know I’ll be using:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly; who errs and comes short again and again; because there is not effort without error and shortcomings; but who does actually strive to do the deed; who knows the great enthusiasm, the great devotion, who spends himself in a worthy cause, who at the best knows in the end the triumph of high achievement and who at the worst, if he fails, at least he fails while daring greatly. So that his place shall never be with those cold and timid souls who know neither victory nor defeat. – Theodore Roosevelt

About Andrea Whitmer

Andrea is a freelance web developer and mom trying to maintain a sense of humor in an otherwise chaotic world. She blogs in hopes of helping others avoid the same mistakes she made in the past. Join in the discussion here on So Over This, or connect on Twitter, Pinterest, Instagram, or Google Plus. You can also subscribe to new posts via RSS so you never miss out!


  1. I am sure that you will be up to adjusting and could make up that extra amount in reasonably short order.  Freelancing for a few hours per day could easily add up to quite a bit of money.  I can get a decent article written in one hour or so.  At $20 a pop, that could add up rather quickly.

  2. Great plan! I'm really excited for you! Although, how do you make so much from this site?

  3. What an exciting day!  Best of luck to you! 

  4. Financial Samurai says:

    Good luck on the new adventure Andrea!  Hope you have a great 2012!

  5. Hey, can I have your boss? She sounds awesome!

  6. Serendipity Savings says:

    Your boss does indeed sound rather quite awesome! Good luck on the freelancing!

  7. You can do it!!  If you need another source of income, try  I made $15/article writing for ehow.  While that wasn't a huge amount, once I got used the the format, I could bang out one per hour, which always helps.

  8. I wish you all the best and hope that 2012 will be a great year for you. Only wish I had so much courage as you. One day…

  9. Sounds like you got it all planned out, Andrea!  You're going to have an awesome 2012!

  10. Tessa@Cantfindcash says:

    Congrats! I'm sure you will do great! I have to ask though, what will happen to your restaurant points?

    • I'll still be doing those. πŸ™‚ I know I'll eat out a lot less since I'll be home, but I still think of it as a problem area. Especially since it's easy now for someone to say, "Hey, let's go out to lunch!" and for me to go, "Okay!" without even thinking about it. So the restaurant points will stick around for 2012.

  11. I'm so proud of you, Andrea, and cannot wait to see how it goes for you. πŸ™‚

  12. AmericanDebtProject says:

    That quote just put tears in my eyes.

  13. Wow, this will be exciting!  Best of luck on your new job! 

  14. You do have a great boss!!  Like I tell my husband (and anyone else who will listen) "I am the boss of me".  Now it is really quite evident that I am.  Who knew?  You are going to do awesome Andrea!

  15. Speaking of being on Twitter talking about movies. Haha.

    I'm in roughly the same boat. I knew that I was losing my job at the beginning of November, so I set forth to figure out how I could write for a living. It presents interesting challenges. But I echo your thoughts on it not being any less stable than working for someone else.

    I've managed to get my expenses down to $385 though. Anything else I spend is for wants, not for needs (i.e. eating out occasionally, instead of cooking for myself). But I know I can get by as long as I have at least that much.

    • Wow, I would kill to have expenses that low! Unfortunately, though, between a car payment and a kid, there's no way right now. I could cut significantly if I had to (my monthly figure includes stuff like my expensive cell phone plan) but I think I can make do with what I've got, at least for awhile. I feel better knowing I have a plan and that I can always go back to a "real" job if I have to. Though I think I'd rather be stabbed in the neck!
      I didn't realize you were blogging full time. We'll have to keep each other posted on how things are going! Hopefully 2012 will be our year. πŸ™‚

  16. Your boss really is the coolest!! I'm so excited for you, and I can't wait to hear more things!

    Also, you make that much money from the site? AWESOME! I really do need to look into putting some ads on mine…

    • If you want more details about that, email me. Don't want to post it out in the open but there are some great ways to make money. Most of my ad income comes from stuff other than the adblocks on my posts.

  17. NetWorthProtect says:

    I like the quote!  I am stating the obvious: Stop smoking!  If your doctor can't convince you maybe a post I wrote a few months ago will:

  18. Oh I know. I've done patches, Chantix, all kinds of stuff… Lost both of my grandmothers to lung cancer. I even consulted a hypnotherapist, but he said it wouldn't do any good until I seriously WANT to quit. And so far I'm not there yet, though I want to get there. If that makes any sense.

    • says:

      I know, easier said than done…  Where I live it is not much of a choice though, cigarettes go for $12 – $15 a pack around here these days.  A pack a day and would be like an second apartment rental…  crazy motivation to stop smoking

  19. The world better be ready for a new blogging giant.

  20. I'm curious will you make a list of things to do when your bored/ or topics to write about?? Seems like after all while you could write all you can write i guess you could also clean the house when you get writer's block lol have fun andrea can't wait to follow you on your journey!

    • I write for several sites besides my own, so I don't see myself running out of writing assignments anytime soon. That said, I do have plenty to do on those off days when there's nothing pressing going on. Like tomorrow, for instance, my son has a doctor's appointment out of town so I'll be gone most of the day. That's the part I look forward to most – being able to take time to actually be involved in some semblance of a real life! For years, my mom has taken care of most doctor's appointments because I had to work. I also take frequent breaks throughout the day to start a load of laundry or play a game on my phone. So it's not a strict schedule as much as a loose plan – I just know if I don't sort of know what I need to be doing, I'll waste a lot of time watching cat videos on Youtube or something.

  21. Lol those cat videos on youtube can be addicting! lol

  22. Hi Andrea,

    As someone who's been self-employed for the past 3 years, the most difficult part of self-employment is making the decision to go solo. Now, I would not trade it for the world. I love being able to get up when I want to, the autonomy and freedom. It's stressful sometimes, especially when the business checking account is looking a little meek, but now I never have to worry about job security or pleasing the boss! 

    I'm excited to see your new creation and I really love what you've done so far with this site. Keep rockin'!

    • Thanks for your input, Jeena! I agonized for a long time, but deep down I know this is the right choice. I just feel like the timing was a little off, financially – I wish I could have waited another year so I'd have more blog income. Still, I think I can do it, and if not, I'll go back to work for awhile and try again later. Self-employment is awesome so far and I hope I never have to go back!

  23. The Girl Next Door says:

    "except I don’t have to waste spend time going to work when I could be writing"

    too funny, I bet there are lots of people who wish they could say the same!

  24. Congrats on becoming self-employed! With the extra time you will have to dedicate to your online ventures, the sky is the limit! I know you can do it πŸ™‚

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