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My Tax Return As A Resume

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tax return as a resume

Last week, I received a challenge from Sandy at First Gen American to participate in her coffee talk series. Sandy is a great story teller and her blog is one of my favorites on the internet so if you haven’t seen it, you should drop by.

Here’s the backstory from Sandy:

You are on vacation and like it happens so often in new places, you meet a deliciously interesting person in your travels. As you learn more about him/her, you find out that not only is this person a bit of an eccentric but a billionaire entrepreneur. You two hit it off immediately and in your chit chat, you discover that (s)he has been looking for someone to fill an open position. As luck would have it, this job is not only your dream job but it’s also in your dream location and at a salary that would allow you to take along your spouse or any other important loved ones if needed.

But here’s the catch.  This eccentric entrepreneur thinks (s)he can learn more about someone from their tax return than they can ever learn from any resume.  You decide this jig is too good to pass up, so you pull out your 2010 tax return, make a copy in its entirety and send it over.  What will your new billionaire friend learn about you and does any of it relate to your dream job? Why or why not?

Mmmm…. What a great story, it makes me want to travel again! I only met poor jobless backpackers during my travels. I guess I wasn’t staying at the right hostel. 😉

So what would my tax return say about me? Now that I think about it, there is a lot of information on the tax return which I would be very hesitant to share with a prospective employer. For example, if I have a big medical expense deduction, it would raise questions about my health and the employer might hesitate to hire me.

We’ll call the eccentric entrepreneur The Sultana for the rest of the story, easier on the tongue.

She will find out that I don’t like to give the IRS free loans because we usually owe them some money. This will be her first clue that I’m a bit tight with money.

The Sultana will know that I am married with one kid and that I take advantage of the Dependant Care Assistance Program (DCAP.) This shows that I don’t like to leave any money on the table.

The tax return will show that we also take full advantage of the tax deferred 401(k) plan. We also invest in the 529 education saving plan to reduce our state tax liability. This means that we are patient and plan for the future. If The Sultana hires me and keeps me happy, then we can have a long fruitful business relationship.

After the 1040, we’ll move on to the schedules. It will show that I am making extra money on the side from my day job. We invested in multiple rental properties and they are generating some income. I also have capital gains and dividend yields. These activities show that I am engaged in the financial market and I am connected to the global pulse. Lastly, she will see Retire by 40 and the modest income generated from this venture.

These side ventures will probably be a negative point for any employer. This shows them that I am entrepreneurial and I am not dedicating 120% to my day job. My current employer would be ecstatic if I worked 10-12 hours/day as there is never any shortage of work (with no OT pay of course.) I used to do that when I started years ago, but now I rarely commit to working those hours. If I were The Sultana, I would make it worth my while to quit these side ventures and commit fully to the job.

Do you think having multiple incomes interfere with the day job? I spend some time checking my stocks almost every morning. The rentals also cause a bit of headaches now and then. Last year one of the microwaves stop working and I spent some office time researching the fix. These side businesses show initiative, but they divide my attention. The Sultana should give me the incentive to concentrate solely on her job. A big fat paycheck and a stake in the company would do it. 🙂

Other coffee talk participants:

Budgeting in the Fun Stuff:  My tax return and me

Dog at My Wallet:   What does your Tax Return Say about you?

Growing my Girls: My taxes my mom

Invest it Wisely: 3 things my tax return says about me

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{ 28 comments… add one }

  • Kevin Mzansi February 10, 2012, 12:31 am

    Really makes you think! What a great challenge from Sandy….

    Reminds me a bit of how in the book “the millionaire next door” there was this one self-made millionaire investor who always asked brokers prospecting for his business to see their financial statements before he invests with them…

    • retirebyforty February 10, 2012, 9:44 am

      That’s a great way to screen financial advisers. I’m a DIY investor now, but if I ever need help, that will be one of my question. I like that book a lot too.

  • Money Infant February 10, 2012, 3:26 am

    I think that taking a break form your day job to focus on other things keeps you fresh and more interested in your day job. Really who focuses 120% on their job for a full 8 (or 10-12) hours? In reality it is a good thing to break away from time to time and let your subconscious work on your job. It helps keep you more creative and productive.

    • retirebyforty February 10, 2012, 9:46 am

      I don’t know if that’s true for me. I think going to the gym at lunch break is a great way to refresh yourself. The side ventures really take a lot of my attention and I’m pretty sure it’s hurting my day job a little bit. That’s ok though, since my goal is go out on my own like you did. 🙂

      • Personal Finance Journey February 11, 2012, 7:17 am

        As long as your employer can’t tell a difference in your performance, you are probably not behaving any differently than other employees. The difference is that your time is diverted by money making ventures while others’ time is diverted by Facebook and reading blogs. . .

  • Dollar D @ The Dollar Disciple February 10, 2012, 8:22 am

    Neat story!

    My feeling is that most employers don’t want entrepreneurial employees, they want employees who are stuck working, and will stay stuck until age 65. Since you’re 37, I doubt most employers would consider you if they found out you owned “RetireBy40.org”. 🙂

    However, since the hypothetical employer is a billionaire and this is your “dream job” I assume it’s a high-level position where your creativity and independent spirit would be an asset to the company.

    • retirebyforty February 10, 2012, 9:48 am

      Most employers probably don’t want to hire someone who doesn’t NEED the paycheck either. That’s too much freedom. My boss would have a cow if he knows I’m running this site. 😀
      It would be great to have creativity and freedom in a dream job.

  • Jeff @ Sustainable Life Blog February 10, 2012, 9:51 am

    Interesting perspective joe – are you sure employers wouldnt enjoy an entrepreneurial employee?

    • retirebyforty February 10, 2012, 10:10 pm

      I think most regular employer would not like entrepreneurial employees. Those people are always looking for a better future and will leave at the first opportunity. 🙂

      • Edward Antrobus February 10, 2012, 10:21 pm

        Whether or not employers like entrepreneurial employees is debatable. But I’m willing to bet that most employers like employees with an entrepreneurial mindset. I’ve tried to be an intra-preneur at every job I’ve had.

      • Tie the Money Knot February 11, 2012, 3:03 pm

        I tend to agree with you that most employers wouldn’t care for an entrepreneurial employee. But, we all need to look out for ourselves!

  • frugalportland February 10, 2012, 10:07 am

    That is a fun response. You really can learn a lot about a person from their tax return! All kinds of things employers aren’t supposed to ask! 🙂

  • cashflowmantra February 10, 2012, 11:35 am

    Interesting discussion to be sure. I am not enjoying thinking about taxes right now, but would probably have a similar story to tell.

    • retirebyforty February 10, 2012, 10:11 pm

      I read about your problem. Sorry to hear that. It’s a huge amount to owe.

  • Edward Antrobus February 10, 2012, 11:45 am

    Well, the first thing they would learn is that I don’t bring my tax returns on my vacation with me!

    But frankly, I don’t buy this argument. What does my tax return reveal about me? Well, aside from all kinds of protected information, as frugalportland pointed out, my tax return would show that that I’ve got a middle class income with middle class debts and savings. Won’t does my tax return not show? Any kind of ability or experience related to the job.

  • Roshawn @ Watson Inc February 10, 2012, 1:25 pm

    Sometimes this can be the case, but my day job does get significantly more than 40 hours a week at times. This isn’t a justification for being divided occasionally, but it does add context: I know I am not cheating my employer despite having other side projects going on.

    • retirebyforty February 10, 2012, 10:15 pm

      That’s good to hear. I don’t think I can multitask very well anymore. My brain just want to focus on one thing at a time.

  • krantcents February 10, 2012, 4:54 pm

    A lot depends on which side of the table you are sitting on. If you are the employer, yes side income means you are probably too independent to be a good employee. On the other side if you are ambitious or just want some additional income it is great. I think the kind of income says a lot about the person. Wall Street investments say one thing vs. a business. A business will take up more time which is a threat to the employer.

    • retirebyforty February 10, 2012, 10:16 pm

      That’s what I thought Larry. I appreciate your comment since you have so much more experience than I do.

  • Suba February 10, 2012, 7:47 pm

    I started writing this post too but couldn’t finish it on time. It is great topic so I might post it when it is done even if it didn’t come on time.

    I can certainly see an employee with a side business as not as devoted to the company. That is why I am trying as much as possible to hide my identity online. Hopefully it will work. I can easily see a person with a side business not giving 100% to the job and at the very least thinking about a bad day at the side job or thinking about how to improve it if it is his/her own business.

    • retirebyforty February 10, 2012, 10:18 pm

      I’ll look forward to your post! I know the side business impact my full time job at least a little bit. I’m sure some people can do both and give 100% to both, but I don’t. Baby RB40 doesn’t help either. 🙂

  • Invest It Wisely February 11, 2012, 10:09 am

    As you might have known, my last employment was against moonlighting, so anything side business-related would have been a negative for them. 🙂 I also know what you mean about that OT with the unpaid hours. At some point you have to decide if you’re going to toil to make another man rich, or yourself.

  • SB @ One Cent At A Time February 11, 2012, 1:06 pm

    Great thought. Hope life is that easy. The name of this blog is enough to keep potential employers away 🙂 good read.

  • What a great topic! I’d be very hesitant to give my tax return because it seems an unreasonable violation of privacy. Would they set my salary based on what my husband makes? As you say, the side businesses could easily affect their opinion of you and how much time you would be able to devote to the job. That part could be discussed without having to resort to looking at your tax return. It just seems a little creepy to me.

  • First Gen American February 12, 2012, 2:43 am

    Great article. I hadn’t even thought of the health angle aspect. Those tax returns really do say a lot about you.

    I also hide my online identity for the most part because I don’t want my employer to think I’m working “part time” at work…which essentially to them is not working around the clock for them.

    But I still see side gigs as something positive to a self made billionaire. After all, that’s probably how they started as well and then one day, one of those little businesses went big. So, I can see Sultana seeing a bit of herself in you and also convincing you to drop the small potatoes side gigs to make real money with her.

    I really enjoyed this series.

  • Elizabeth @ Broke Professionals February 12, 2012, 1:53 pm

    That rocks that you use the 529 based in your state and get the tax break that goes with it. The state in which I reside doesn’t have one of the top-performing 529s, so ours is held in another state – which means no tax benefit 🙁

  • Elizabeth @ Broke Professionals February 12, 2012, 1:54 pm

    I’ve read a couple of other sites doing this series, and they’ve all been so fun to read. What would my tax returns say about me? With Three 1099s filed last year, definitely that I’m maximizing my opportunity for multiple streams of cash!

  • Robert @ The College Investor February 12, 2012, 4:54 pm

    I think the point about your multiple incomes and what an employer might think is interesting…you really think they would doc you?

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