The Thing About Growing Up That They Don’t Tell You in School

Somehow, I’m turning 31 in two months. Wasn’t I just turning 30? Wasn’t I just turning 21? And all that time I had the thought implanted in my head that I was so ahead of so many others because I had a career and didn’t have kids or a husband of my own to get in the way. Those come later – like, once you’re old enough to really have a kid and a husband. I don’t know when. Just later.

With the exception of a few women I grew up with and know who are my age, most have at least one child by now. Many have two. God help me when they start on their third and I’m still not married yet. I’m just in this mega rut. Why can’t I focus at my job? Why can’t I believe in myself enough to get another job? I just feel like I’m living all of this life for absolutely nothing. Of course one needs a job and money to have kids, so there is that. But I don’t know about how to go about a life where I both want to be a mother and be a working woman… when I don’t even really want to work… and I don’t even really want to not work.

I don’t enjoy sitting around on my ass all day doing nothing, despite being awfully talented at it. But I also don’t enjoy spending my life trapped in corporate hell tearing my body apart with stress to promote some product that often times isn’t very good in the first place, so someone else can likely get rich off of it. This is life I know, and a very privileged one at that, and I should stop complaining. But suddenly those stars on shows like Teen Moon and 16 & Pregnant seem to have it all figured out. Meanwhile I’m just wasting away with no purpose. Woe is me, I know. But it makes me so depressed. It makes it hard to do anything at all. And I can’t believe I lost a really good job because I spent too much time worrying about wasting away my life. Well, now I’m wasting away my life and I’m not making any money. That’s not really any better, is it?

I’ve done good work before, I have. But every interview I have is filled with little white lies. They often get called out. I lean on my improv training to bs this or that. I know that I shouldn’t be hired. I worry about not being able to fulfill the job responsibilities. I worry about starting work and then it going so well that I put off having a family for another few years until it’s too late. And no job is really going to be better than my last one… I had such a great opportunity and I blew it. The company wasn’t perfect but no company is. I am the one who blew it. And now I have to deal with the repercussions.

Yes, I’m getting interviews, or at least a couple of them. One this morning I wanted to just stop in the middle and excuse myself from the application process because I just don’t have work samples to support all those things I had to say I’ve done before to get the interview in the first place.  Then the one company that really wants to hire me wants me for the most senior role of all, one I’m ill equipped to succeed in, one that I want but one that I want in about 10 years when I’m actually ready for it and by then god willing I’ll have two children and won’t want to spend all my time in upper management and never see my kids.

Part of me wants to just apply and hopefully get some basic administrative role. It won’t pay as well at all and I haven’t been that great at administrative work previously, but maybe now I’d at least appreciate it more. I just wish I had someone to talk to about all this, someone who could provide good advice but also who isn’t delusional about my actual abilities. I just feel like everything is falling apart, no more than normal except the slowly draining bank account, but I just can’t deal with it all. So I get further depressed. I start thinking about how lovely it would just be to disappear right now because no matter what I’m going to fail.

I understand from the outside that sounds dramatic but it’s reality. People want to hire people who can come up with things to do and get them done. I can’t do the first part. I have no confidence. My parents taught me to doubt myself every possible instant I could, and I still do. I wish I knew what it was like to feel confident, like I could be successful, like I deserved anything at all that I have. But all I feel is hopeless. Incompetent and hopeless and miserable. So what I wonder is, what is there that I can do where I can make some kind of money to survive and also consistently offer value to an organization? Is there anything I can do? Is there anything I won’t mess up?

Which Way to Go? The Career Ladder is a Maze

Throughout the last 10 years of my career, give or take, I’ve basically just gone where the wind blows. Each job I’ve obtained was the only option I had at the time. I’m not being overly dramatic here. I would interview for dozens and dozens of positions and finally when someone gave me an offer I’d take it. I didn’t really have the luxury of deciding what to do or weigh two or more offers against each other. I either accepted the offer presented or I waited weeks – months – years – more to get another offer. Waiting just wasn’t worth it.

All of that has left me in a career which — while I’ve been able to earn and save money — hasn’t shaped up to be a good foundation for whoever it is I want to be. It also hasn’t provided the experience needed to put me in that much of a better position each time I’m back on the market. That’s finally starting to change, but I still have yet to land an offer.

Right now, I’m extremely confused about what I should do next. I’m interviewing for very, very different positions in companies ranging from 25 people to 1000. Some of the roles have the potential of a VP titles, other director, and others manager. Part of me says “go for the VP role now” while the rational part says “you are not ready to be a VP and this is the time in your life when you should invest in being a manager for a larger, stable company to learn how to do this stuff right and/or broaden your skillset without everything being on fire all. the. time.”

I don’t have any offers yet, but I know that part of getting an offer is really wanting the role and pushing for it. Right now I’m interviewing for three positions and I just can’t make up my mind which one I would want. The VP role not only is a very senior position, but it also is with a company that is doing something really interesting and that excites me. But being a VP in a small company and having to build out an entire team while also executing on the day-to-day is probably too much for me right now. All I really want is the chance to focus on something (partially due and partially what I’ve done before) and do it well while learning how to do it better. A VP position will not provide that opportunity. I just don’t want to waltz into another failure. I have ideas of what I could do in order to do a good job, but I can see myself getting overwhelmed again.

But on the other end of the spectrum I could be very bored at a slower moving, larger company. Right now I think slower moving would be a good thing for me, but I’m not sure how long of that I’d be able to thrive in. I tend to do well in fast-moving environments, just ones where I don’t have to manage, build teams and execute all at the same time.

Then there’s the question of whether I stay in my specific area of my field or move into a tangential one, if I can get such an opportunity. I’m torn about that as well, although I’m comfortable admitting that I want to be closer to the product vs the more buzz side of marketing. Getting new customers is a useful skill but it’s a never-ending and impossible-to-win game. Meanwhile, figuring out what a market wants and determining how to tell the story of a product is at least intellectually stimulating and offers new challenges vs the same ones each quarter only bigger.

I mean I value this area of marketing a lot but I do not want to spend the rest of my life praying night and day that a reporter will decide to write about my company or testing the color of a button on a website to see – not if a product would be able to be used better – but if a few more people would fill out a form to contact a sales team. Again, I highly value the people who do that but I do not want to spend the rest of my life doing it. I’d rather be working in product but that’s a challenge given I don’t know how to code, so the next best thing is product marketing. That’s an area I can see myself really excelling in. And I’m looking to take a lower-level role in an organization to focus on just that. Yes, it also includes a lot of the less exciting dirty work (making dozens of datasheets for different industries, et al) but at least you get to be part of defining the story of a product and why its new features are valuable. You don’t just rehash the messaging someone else came up with. That’s the mind-numbing part of PR.. you’re a professional megaphone, and I don’t want to be a professional megaphone the rest of my life.

That said, I don’t have any offers yet, and eventually I might have to revert to megaphonism if that’s the only role I can get.


10 Tax Breaks That Only The Rich Enjoy

Ahh, what’s that smell? American Greed?

We 99%ers love to call out the 1%. Some get to the 1% with hard work and luck, but many are placed there due to being born into privilege and likely a sizable inheritance. Others weasel their way into wealth. Few can get there in a way that wouldn’t make some “kooobaya-type god”scream mercy. Regardless of how the 1% made it to the top of the fiscal food chain, they can enjoy a whole host of benefits staying there — private jets, beautiful women, more beautiful women, houses, yachts, and — last but not least — some really tricky tax breaks so they can just keep accumulating more and more wealth!

Here are 10 tax breaks that only the super rich enjoy. Read ‘em and weep.

  1. Income Tax, Smincome Tax
    The rich don’t need your stinkin’ income. CEOs can come out and say they’re going to take a $1 salary and the masses think that they’re being just so damn humble and giving. Not so. While us lowly folk have to work and get paid salary to do things like eat and have a roof over our heads and pay for our kids piano lessons, the rich can take their heaping savings and put it into investments that compound over time. Good thing these folks are not actually earning any income because that means they can enjoy 0% tax rates on all of their capital gains. The best us lowly folk can do is attempt to put together an investment plan that eventually provides us with enough dividends and capital gains to also take out our money tax free, even if we never have an army of beautiful girls/men and/or private jets (source)
  2. Taxes Are for Losers (AKA Poor People)
    Some rich folk work in fields like investment banking, private equity management, or real estate partnerships. Not only do they get paid a lot off the bat for these roles in terms of total compensation, their pay is not in the form of that same lowly income you and I see deposited into our bank accounts every few weeks. These modern-day royals get to be paid in a “carried interest” which is – somehow – usually taxed as a capital gain instead of ordinary income. That means these richies are paying 20% taxes to the federal government on all of their earnings. Even Mitt Romney managed to pay 15% taxes for his great service to our country as head of Bain Capital (yea, aren’t you glad he didn’t become our president?) (source)
  3. Home is Where the Cash Is
    The government wants to encourage home ownership because this means the country is more stable, generally speaking. Thus, big brother provides tax incentives for home owners of all wealth levels (as long as you can afford a house.) However, the best writeoffs go to the super rich. The mortgage interest deduction lets taxpayers who itemize deduct the interest they pay on their home mortgages. The way the program is set up, the more expensive the home and the higher the homeowner’s tax bracket, the bigger that subsidy is. (source)”Less than one-third of taxpayers are able to take advantage of the deduction—it is restricted to those who itemize their deductions, a group that skews toward the upper end of the income distribution. Also, the benefit is tied to the marginal tax rate of the taxpayer and so has higher value to those with higher income. For households making above $200,000 a year, the average benefit is $1,784 a year in tax savings. For households earning $65,000 a year, the deduction generally yields less than $200 in tax savings.”  (source)
  4. That Foggy Definition of Charity the Rich Love
    Oh, what wonder, a 1%-er is donating something to charity. That’s great, if genuinely done to help an organization, but often the reason for donation is not exactly out of good will. It’s horrible to say but many charities are corporate scams. Seriously. Let’s take a look at Walmart. The Waltons, owners of Walmart, are using “Jackie O” trusts to both give money to charity AND pass on money to future generations without paying estate taxes. Oh, and did I mention they’re doing this all through their own charity, The Walton Family Foundation? This is perhaps more disturbing than the other tax loopholes because wealth dynasties are why inequality is cemented into American culture. (source)What’s more, “generally, you can deduct the fair market value of property you donate to charity if you’ve owned it for more than one year and the property is used to further the charity’s tax-exempt function. Thus, the appreciation in value is untaxed forever. The tax law limits the annual deduction for gifts of appreciated property to 30 percent of AGI, but that still provides a gaping tax loophole.” (source)
  5. Beam Me Up and Around and Around Scotty
    Geez, private jets are just so damn expensive. But how else are the rich supposed to get from point A to point B? Not with the underlings, by god. There is a special subsidy for corporate jets which cost taxpayers $3 billion a year. Yes, a common tax trick and CEO perk is to pay for private jets under the guise of security (because what if a poor average flight attendant accidentally spilled coffee on their Prada suit during a turbulent flight???) If a benefit is classified as for security purposes the CEO will pay a reduced tax bill or no tax at all on the bene. (source)
  6. Mooooooooooooooooooooooooooooo. Mooo. Mooooney
    I feel like we should just let this tax write off slide for the sheer fact of it being so ridiculous. JK. This will make you want to go tip some cows. In states like New Jersey, Florida, Texas, Iowa, Colorado, Alabama and more, farmers can take a tax deduction for their service feeding our great nation. That is, even farmers that aren’t farmers at all. According to an article in The Nation, that’s what Michael Dell did with his second home—a suburban ranch in Austin. Because he hunted there periodically and maintained a “well-managed deer herd,” he was able to reduce the property’s 2005 market value from $71.4 million to an agricultural value of $290,000. That saved Dell—but cost Texas—$1.2 million. Florida has a well-known “rent a cow” program (I kid you not.) What is this cow business? To qualify for the tax writeoff, Florida requires a couple of cows or a herd of goats, which don’t have to be on the property all the time. So you have wealthy people paying next to nothing on property tax because they own lots of acres and can afford to rent a few cows.  (source)
  7. John Edwards and Newt Gingrich Walked into a Bar (and didn’t pay any tax)
    This one is a doosey and surprise surprise it involves politicians again. Slime of the earth. Payroll taxes are supposed to be paid on income from work, with social security payroll tax paid on the first $113k in earnings (as of 2013) and medicare payroll tax paid on all earnings. Except S corporations, which are made up of a partnership of self-employed type folks, don’t need to qualify all their earnings as payroll, and thus it doesn’t need to be taxed. This one gets a bit complicated to explain, so just check out this writeup to get the full picture of how dishonest richies can get away with legal tax loopholes that only benefit the 1% (source)

    • Newt Gingrich: In 2010, Gingrich Holdings, Inc and Gingrich Productions paid Newt Gingrich$444,327 in wage income while declaring $2.4 million as profits of the S corp. This allowed Speaker Gingrich to avoid $69,000 in Medicare payroll taxes. [Wall Street Journal Market Watch, 1/23/2012]
    • John Edwards: Senator Edwards earned $26.9 million from his work as a trial lawyer in 1995. He paid himself a salary of $360,000 each year for four years and took the rest as distributions from his S corp. This saved Senator Edwards an estimated $600,000 in payroll taxes. [New York Times, 7/10/2004]
  8. Selling a House and Paying Taxes?  Yea, Right.
    Even average American homeowners can take $250,000 of their home price increase tax free ($500,000 for married homeowners) which is a pretty good deal after years of fixing broken air conditioning systems and having termite genocide parties. But the real tax benefit for housing is only available to the super rich (surprise!) A 1031 Exchange, also called a like-kind exchange, enables real estate investors to trade the equity in one property to another property of equal or more value without having to pay taxes (yes, you heard me right.) The taxes will need to be paid eventually, but the investor, in the meantime, gets to reallocate their portfolio and you can still take a depreciation tax write-off on your properties that are being exchanged. There’s no limit to how many times you can do a 1031 exchange. Since the rich are doing this with their real estate investment property (you can’t do this with personal property, sorry 99%), when they do sell it eventually they’ll sell at the capital gains rate. (source)
  9. Tax Breaks (i.e. Itemization) Seriously Favors the Rich
    There are many different tax deductions available to take. But, of course, in order to take a deduction, you must itemize your taxes. While itemizing makes financial sense for high-income Americans, it does not for low ones. This means that deductions are mostly utilized by the rich. Only about one-third of Americans itemize their deductions, and they are mostly the well off. In 2010, only 29.3% of those making between $30,000 and $50,000 itemized, but 96.8% of those making $250,000-plus did. (source)
  10. One Home is Just Not Enough
    Speaking of itemized deductions, owners of two homes get to write the mortgage of their second one off as well, as long as they itemize. It turns out this tax benefit isn’t for folks who own tiny little vacation bungalows by the shore or middle-class lakeside cabins. Nope, the main benefactors are the super wealthy. Just to rub salt in the wound of us reg’ies, rich folk can DEDUCT THE INTEREST PAID ON THEIR LUXURY YACHTS (fyi that clink-clanking you hear is the sound of me kicking all the buckets in the world.) As long as these boats are equipped with sleeping quarters, a kitchen and a toliet they can deduct the mortgage debt on these “homes.” (source)


How to Estimate Your Tax Rate in Retirement

As I’ve been running calculations on whether or not it makes sense to do a Roth Conversion, I came back to the question — what will my effective tax rate be in retirement?

That’s a question a lot of us considering a Roth Conversion should ask, but it’s not one that is easy to answer. What’s important, though, is that the numbers you plug into your calculations are reasonable. After all, expecting a 40% income tax in retirement each year can greatly skew your calculations if in actuality you’ll see a 20% effective tax rate.

This Forbes article by Erik Carter was really eye-opening: Why Your Taxes in Retirement May Be Less Than You Think

Article Highlights 

  • You are probably overestimating what you will have to pay in taxes at retirement
  • Withdrawls from Roth accounts are tax-free at 59.5
  • Social Security is taxed at ordinary income rates but only part of it is taxable
  • Long-term capital gains are taxed at lower rates than income tax (*at least according to current tax law)
  • Your income will probably be lower and put you in a lower tax bracket (i.e. experts recommend 80% of your pre-retirement income, but you may need less)
  • When you are older than 65, you get different deductions than younger people. For instance, you have a $1550 higher standard deduction than us young folk
  • A lot of 401k contributions withdrawn yearly will be taxed at lower rates, especially if you plan on taking out less than $36k per year (note, that’s no where near 80% of my current salary, but I could live on it in another state if I owned a house free and clear)
  • Tax rates could be higher when you retire but that’s unlikely (*not impossible)
  • Lots of people retire in states that don’t have income tax like Texas, Florida and Nevada. (*check out this handy-dandy state income tax calculator and weep… unless you live in a state with low income tax.)
  • Move where all the old people live and you’ll be fine.

Is it Impostor Syndrome or Just ADHD Reality?

Another interview, another scrunching up my face in horror at something all too honest that I say as I’m asked about my experience and weaknesses. But let’s be real – if I were a hiring manager for most of these jobs I would not hire me. The few that don’t see this during the interview process – the only ones who would ever offer me an opportunity – are inexperienced in hiring or somehow unable to see the truth. It’s not just impostor syndrome, I’m just not that intelligent or reliable. Occasionally I have a brilliant idea and execute well, but most of the time I just get super anxious and waste time because I’m too scared to make decisions. Sometimes I come to work late because I’m depressed and have trouble getting out of bed. I can’t multi-task because having too many things to do at once and too many decisions to make equals one very stressed out and unproductive me. This thread really says it all.

So how am I supposed to convince anyone to hire me? I just look around at all of my peers in the business world and most of them just have their shit together. Some are really smart and able to get stuff done like superheros. Others are just able to execute really well, communicate goals and exceed them. All of this, others say, one can learn to do. Anyone can be on top of their shit. Anyone can learn process and get stuff done. Anyone can make decisions, test ideas and pick the best ones to continue with. Anyone can do this – except I can’t. I just can’t.

I don’t know where to go from here. Even starter interviews for junior-level positions somehow seem to end with “you’re not experienced enough.” That is after 10 years in the workforce. I’m not making this up. And it’s true — I have such a smattering of experiences but no one solid skillset that fits any job description. Ultimately it doesn’t matter anyway because if I did get a job I’d just end up disappointing them. I really don’t know what to do.

I am fortunate in that I have a good amount of savings to survive on for a little while, but eventually I need to get a job. Junior level roles, if I could get one, often require more of the detail-oriented work that I’m bad at due to my ADHD. But senior level roles still require the ability to be detail-oriented and set bigger picture strategy while ensuring the day-to-day gets done.

Interviewing is awful. I’m sure it’s wonderful for people like my friend who are just so good at what they do and know it. Everyone who interviews him falls in hiring love because he’s just professionally perfect, from his Ivy degree to his experience and contributions to all his companies along the way. I’m happy for him, and for my other friends who are doing well professionally, but also jealous, jealous because that will never be me. I can maybe fake it for a month or two but it won’t last.

This is why I think I really should leave business… but I’m not sure what else out there I can do. I feel like somehow I have a bit of intelligence inside my crazy distracted head but that’s worthless with all of this anxiety and inability to execute. To whom this may concern, please don’t hire me, I’m a hot mess.