There is No Answer to this Riddle

While I’m feeling confident about the next step in my career as a whole – given I’ve now had appropriate time to rest and reset prior to taking another position – I’m still extremely confused about what to do next. It seems I will indeed have the luxury of at least two options, but I’m just completely torn on which opportunity to sign up for. On top of that I’m severely stressing out over negotiations. I just wish one employer could give me a deal that I cannot refuse, but of course job negotiation doesn’t work like that.

I don’t want to go into this position as a short-term fling, so to speak. Wherever I go next I want to stay at least a year and ideally remain until I have my first child, or after that if it makes sense. I’m turning 31(!!!) in two months. My plan is to get married at 32 and have my first kid by 33 or at latest 34. So. I can go to a company that may or may not be around in two years now, work my ass off, negotiate a high enough salary to save a lot of money, and take time to be a mom when the company either is acquired or goes under. I would need to set up my contact so the company’s success does not inhibit my ability to achieve this plan. Yet I’m not sure if this makes sense at all.

Beyond professional objectives, my financial goals are to achieve $400k in networth in 2015 ($15k-$30k in investment growth + $70k-$85k in additional savings.) I can live on ~$3500 a month (less if needed, but let’s just say $3.5k to allow for some vacations and shopping sprees, which I tend to take when I’m stressed.) So in order to save an additional $85k I need to be able to put away $7083 a month after taxes. That’s a lot and probably not possible, realistically. I would have to make $10583 AFTER taxes in order to do this. Well, if I make $200k a year that’s really $8938 a month after state/fed tax (estimate.) I mean, $8938 a month is a lot (not that I’m getting $200k a year, but I’m just saying my goals aren’t realistic, unfortunately.) But – let’s just say I an earn 10% on my existing savings for the year — that leaves $70k to save for the year or $5833 per month. That would give me $3105 a month for rent/food/life and I could deal with that — if I was making $200k per year. That sounds like a very lot but given my aggressive financial savings goals it really isn’t.

My objective is to get to $500k networth before I have my first child. That has been my objective throughout my 20s and it hasn’t changed. Given I’m 31 now I’m thinking about that a lot. I’m not going to chose a job just because of this, but every extra few thousand dollars I can negotiate gets me closer to this goal. Maybe I can reach it. Who knows. It’s not like I won’t have a kid until I do, but I like to set goals for myself and achieve them. I want to hit $500k by the time I’m 33. Given some of the job offers I am receiving this no longer seems entirely impossible.

But ultimately there is more to selecting a job than salary. I want to find a place where I can do a great job – where I will learn and grow and ultimately have a sustainable career, not just a few years of high-stress before I’m thrown to the dogs. I’m so lucky to even have these opportunities but I want to pick the right one. And both are just so very different. I really am excited about the opportunity of teaming with a very smart former colleague and another good friend of mine as well as a prior agency I rock and rolled with at a previous co, but I’m not sure that will be enough to win tenure at a rocky company. Its further grace is that I absolutely love the general space the company is in. On the other hand I have a relatively stable larger company with a role that isn’t as high up but where I would be… well… both probably more stable but also more bored. As I think about it I believe I can still go to the larger company a few years down the line as these talented folks don’t jump ship often… some have been in the company for over 10 years. If they like me now why wouldn’t they like me later? I’d just be gaining more relevant experience before coming back for another shot.

Or do I stop going with my gut on these things and maybe for once think this all through? I just wish I had someone who has been in this position before to talk about this with. Honestly I am considering hiring an attorney to help with contract negotiations. S/he won’t help me decide what to do, but at least I can negotiate the best deal for myself and perhaps de-risk the riskier option a bit. I am surprised by how confused I am by all this and it sounds crazy but I wish I could do BOTH jobs. Well, maybe I can, just not both at the same time.

Opportunities and Decisions and Uncertainties

Job hunting seems to either feel like a drought or a flood. This week I have had so many interviews I cannot count them both hands (though to be fair a number of them were with many people at two different companies, but still.) While I don’t have any official offers – yet – I feel pretty confident that both of these are going to come through (though I really don’t know how the offers will compare or if they’ll come in at the same time… the smaller company is dragging out the hiring process despite, I think, making it clear they want me for the role, and the big company is just moving slow like a big company does.

That said, I’m incredibly torn between these two opportunities. They are just SO different that it’s hard to compare one to the other. The offer and package will definitely influence that (esp if they are drastically different) but ultimately I want to go somewhere that will be my next mid- to long-term thing.

Part of me feels like now before I have kids is maybe the last time when doing a smaller company makes sense, and it’s more a turnaround than startup so it’s a new type of challenge and one I actually think I’m quite suited for. The culture is definitely quirky in all its glory and oddities, but I’m quirky so that probably is mostly a good thing. It would mean working very long hours for the foreseeable future but also potentially really making a huge difference in the business. I keep coming back to the reasons for my last gig not working out and that largely had to do with my inability to get excited about the product — it just wasn’t applicable to enough people in the world, nor did it really improve the world at all. It was a product designed to make money – which all products are – but it had little else going for it in the “help the world” scenario which makes my professional heart sing.

I need some story and interesting space to sink my chompers into. And this smaller company definitely has that. It’s risky in that if I don’t do my job well the company could not grow according to plan and I’d both be out of a job and be responsible for its failure. Meanwhile, the larger company is not an easy role either. It would be very challenging as well, though for different reasons. I surprised myself in how much I enjoyed meeting with the team at this public company, and while I don’t know the results yet I feel like I performed really well in the interview. While often when I interview at smaller companies — who want someone who can do just about everything — I have to stretch the truth a little bit to fit their ideal superwoman, in a bigger company I can just be myself. There are plenty times when that self doesn’t fit a role, but when it does it just seems to click and I feel confident that I’d be going into a position – and surrounded by a team of coaches and peers – who can help me get even better at what I do.

That said – there really is plenty of time in my life to go to a larger company where I don’t necessarily have to stay at the office until 7 or 8pm every night. And in the smaller company there’s still upside, not that I ever expect private company stock to perform well, but the real upside is having a second solid success story – and while I want that to mean that the company does extremely well and everyone is rewarded – it can also mean a lot of other things, as long as I do my job well. I have to just accept that there are a lot of factors I cannot control which effect the outcome – but I can play my part and play it very well. I can bring on top talent to help me (hopefully, knock on wood) and really make a huge difference. Perhaps I like the turnaround better than the startup. There’s a little safety in everyone being more realistic than folks are early on when a company is just launched and product-market fit hasn’t really been defined yet – although the absolute worst thing you could do is even think this when your job is to make everyone want to buy this product.

Even in the case of a new company with really smart executives odds are they’re going to start with a product that won’t look much or anything like what the product is a year or two later. Pivots, even subtle ones, are normal and acceptable. But if you’re in marketing you have to be full speed ahead even if you have a hunch that change is coming soon. Now, this happens in large companies as well, and it can be so jarring because transparency or cross-functional communication isn’t as commonplace as in very small companies. It’s just that in large companies there seems to be a buffer of time and a team to get you motivated on telling one story that might shift a quarter later, vs being on your own in a team moving a thousand miles a minute. Neither world is perfect, they’re just different.

However in certain turnaround situations you have a company that has been through a lot of the back and forth and has found market fit. This is an ideal opportunity to come in, especially for me personally, because what I do best is helping generate consensus around product story and then taking that story and strategically blasting it to the world. Of course this is not going to be an easy path either — a turnaround is simply on its way up, and often in business, as in gravity, what goes up must come down. But unlike gravity, in business, it can go up again. And down again. And up again. That’s business. Even if no one IN business wants that to be the case.

I like the turnaround role to because you have the opportunity to come in and remind everyone — whoever has hung on through the rollercoaster to get the company where it is — that they really do have something great. It’s not a “savior” role per se, but it is a role that is often greatly appreciated because people like cheerleaders… with brains… who can help them take all of their hard work and get everyone, internally and externally, excited about it. So it can be a really fun point of a company to come in. You get to skip the early rollercoaster but you also don’t get stuck in large enterprise politics and layers of management.

But have I convinced myself this is really what I want? It will admittedly be hard to turn down the larger company which – in many ways is a turnaround story in itself – for a smaller company that is much lesser known. At the moment EVERY SINGLE COMPANY on my resume no longer exists, or probably won’t exist soon. That really is not a good thing. Even large company I worked for was acquired with its brand dissolved. Who wants to hire someone with that sort of track record? Having a few years at a company that will probably be around for many years — and doing well at that company with good references there — may be worth a heck of a lot at this point in my career. Plus the vibe is just so different. I have quirk central as one option and level-headed sanity in the other. The two potential opps are seriously night and day — and I could see really enjoying and doing well in both, for different reasons.

I guess at this point I just have to wait and see if I actually get either offer… I tend to have a good sense about whether or not I knocked the interviews out of the park… I could be way off. In each company there was one very challenging interview. In the smaller company I could tell one of the VPs just didn’t like me. He didn’t say quite as much but he just kept criticizing everything I said, which I understand to a point, but it didn’t leave me with a great taste in my mouth for how we’d work together if I were hired for the role. Meanwhile in the larger company one of the senior team members threw a bunch of hard questions at me and I really nailed it. I could tell he was impressed and I think shocked by how I could basically speak the messaging of their product passionately without being a member of the team. Luckily the topic was a space I’m somewhat familiar with but I do seem to have a talent for spin — at least when I actually believe in the product or the vision of the product.

In both of these cases I do care about the product areas… maybe one a little more than the other given its actual ability to benefit society in addition to make companies more money… but really both have elements of societal benefit and are more about the end user experience the user benefits than optimizing process. Hmm. That’s an interesting thought as even though products can both optimize process and provide end user benefit I prefer to work for companies that are focused on the end user benefit versus just increasing efficiencies  alone. There needs to be some sort of “person” that’s part of the story… not just the person who is getting better results because they’re using a product… but the person(s) who are being improved and having their lives improved by using the product. Anyway, both companies cover this requirement, so I guess I have to just wait and see which if either I get offers for. I have a few other potentials in the works as well… when it rains it pours… but many are for companies where they’re focusing on process optimization vs people, so I can’t see myself excelling there over the long term. I want to be smart whatever I choose this time – it’s not just about the paycheck… it’s about where I can really blossom and help and organization blossom as well.

#WhyIStayed – Growing Up in Domestic Violence

There wasn’t just one incident that stands out, one knock-out punch or fatal wound, but my childhood was flooded with ongoing domestic violence, and for the most part I blamed myself for all of it. Even though I’ve gone through the story a billion times in therapy, perhaps I haven’t really processed what this has done to me psychologically. The terrible anxiety, overwhelming fear of failure, being so depressed ALL. THE. TIME., being unable to accomplish tasks that should be easy because my mind is a big mush pile of terror. Yea, maybe growing up in a house of abuse has something to do with that.

Since the whole Ray Rice scandal — where he knocked his fiancee out cold in an elevator and — oops, got caught on camera — domestic violence has been a hot topic. So has the hashtag #whyistayed where women are posting on twitter why they stay in relationships where they are abused. And, yes, men are often abused as well, so let’s not forget that. Regardless, of the stories out there about domestic violence one that I read talked about a woman whose friends asked her if her husband “hit” her and she said no (but he shoved her and bit her and even broke her wrist.) Not everyone is a puncher.

I feel bad for my father. He grew up in a working class family, the oldest of six. His father had a temper and a hot fuse. Since I can remember my dad has been morbidly obese, slodging to work an hour on the train five days a week, getting home after sunset with barely any time to see his family. So when he came home and my mother stood at the door complaining about how I didn’t clean my room or I wasn’t doing my homework, he got angry, very angry. If I did something “bad” enough I’d get a quick strapping and go up to my room to cry it off and tell myself how horrible I am over and over again. Then would come the fighting. My mom would tell him that he didn’t HAVE to beat me for it. He’s get extremely angry at her for suggesting that, as she went to him to solve the problem and in his mind he solved it. Or they’d be fighting about something else. I really don’t remember a day going by when they weren’t fighting.

Most fights were benign. They’d yell for a while, her in her high-pitched voice, him low-pitched and fuming. Eventually the noise would die down and I’d fall asleep. Then there were other nights… or weekends, when there was more opportunity for an eruption… when things got uglier. At some point I’d walk downstairs to try to stop them. I remember once walking between my dad and my mom and telling him that if he wanted to hurt her he’d have to hurt me first. He usually stopped then, and acted as if nothing happened.

When the worst fights occurred I wasn’t around. Once, he shoved her so hard that her glasses broke. Actually, I recall her telling me he had done this before – on their honeymoon. He’s caused her arm to bruise numerous times. He doesn’t think he abuses her. He thinks everything is her fault. And I think it’s all my fault. Well, not so much currently, it can’t all be currently as I moved far away and don’t tell them about my problems. On the phone the other day my dad could sense sadness in my voice and he said “are you doing ok, you sound sad” to which I replied “I’m fine.” There is no point telling them the truth. Removing my drama from their lives doesn’t stop the abuse, but at least I can’t feel responsible for it.

I was afraid that one day I’d come home and I’d find my mother dead. I knew that my dad would never mean to kill her. He wouldn’t get a gun or a knife or anything and plot her death. But he’s a big guy and she’s rather small. It wouldn’t take much for him to accidentally break her neck. I tried not to think about it. But the reality was you can’t just not think about this stuff, even if you’re not thinking about it, even if you are convinced that it is all your fault.

So now that I’m this 30-year-old adult and fucking up my life by being unable to maintain a job and get stuff done, now that I’m supposed to be self sustaining and prosperous on my own with a stable, full-time role where I can use my mind to make shit happen, I just fall apart. The saddest thing of all is that the only role in my life that I’ve ever done somewhat well in was one where my boss was rather mean to me and degraded my work. But he provided the structure I needed to succeed. I felt comfortable in that environment, go figure. He knew it too. And I worked my ass off and you know what, I did a really good job because I wasn’t trying to be great, I was trying to be good enough. And I needed to know that I wasn’t good enough and what good enough was so I could strive to be it. As soon as I was in a role where my boss was a sane, nice person, I fell apart. That makes me really sad. That makes me scared about my ability to succeed in any role in the future.

I don’t want to put all of my work issues on this, but what I can say is that growing up in an abusive household really fucks with your mind and your sense of self worth. I know a lot of other kids had it a lot worse than I did — I’ve heard horror stories of much worse abuse, alcoholism, molestation, etc, and I had none of that. My family was sober and made decent money and we lived a comfortable life, with the exception of all the fighting. I just need a way to get past all of it. But the reality is my mother is still with him after all these years. He’s dying of cancer and he won’t be around much longer so she wouldn’t leave him now, but somehow he still finds it in him to call her stupid, to belittle her, to shove her on occasion, to do everything to humiliate and degrade her and treat her like a piece of shit. And I’m trying to find a way to make peace with him and all of this before it’s too late. I just want to move on so I can be a real adult. So I can have a family of my own. So I can do well in my job and not feel like I need permission to be successful and happy. I don’t know how though.


Unemployment Continues: The Ups and Downs

Today, I’m feeling optimistic about a few job opportunities which may actually be real. Well, I’m excited about one in particular but also terrified of it. I’m the closet to getting that one as well. Whatever I do I want to kick major ass at it. And I feel like I’m finally rested enough and in a good mental state to succeed, but I know with that mental state it isn’t likely to last long. However, I just want to get this job and move forward with my life. But still ahead lies all the negotiation and such, if I get an offer. And we all know how much I hate negotiating for myself.

That said — I am getting excited about this potential. I realized that what’s most important is that I work for a company where I’m passionate about the product and the purpose it serves. In this case I’m definitely passionate about the product’s purpose – while it’s still a business it does ultimately help society and I think that’s going to greatly effect how I feel when I wake up in the morning for another day at the office. Sure the typical laws of business still apply and if I don’t succeed at the business side of things my do-gooder sentimentality won’t really help much,, but at the least it will keep me enthusiastic during any tough business times.

In addition to the job possibility, there is a decent chance a good friend of mine who is very talented will leave his current role to consult for my team. This would be absolutely amazing as we complement each other well professionally and he is one of the hardest working people I know who is also really, really good at his job. I think as a leader no matter how good you are individually your success is largely dictated on how well you attract the best people. I’ve had trouble with that as I’m socially – uh – abnormal – but on the rare occasion I make a friend who clicks with my working style as well. Even though I’m not sure if this will all play out for many reasons, I’m looking forward to the possibility of working with him again and mind melding to do some brilliant work and really help a business grow. I can’t do it on my own, that’s for sure. Talent is hard to find, esp talent that knows how to get stuff done and get the right stuff done.

So I guess I’m in a really good mood right now… with all the potential for this to work out. But I’m nervous about everything until negotiations are done and paperwork has been signed (as I should be.) I might be able to get everything wrapped up this week, take my two week vacation and come back to town with a job and a start date (wouldn’t that be awesome and just perfect?) Well, we’ll see, but I’m trying to stay positive. I don’t want to invest too much time in prepping for this role if I’m not going to get it — and I need to also focus on the other roles I’m applying for at the moment — and applying for others if nothing else pans out — but I just have a good feeling about this. I just hope it works out.

Marriage Tax Penalty: Is it real? (*Hint… Yes it is)

My boyfriend and I have been dating for over eight years now and we’re seriously discussing marriage. I’m not sold on the whole marriage thing — I don’t believe one needs to be contractually committed to another person to have a lifelong partnership and a family. It seems that with all of my passionate hatred of organized religion and government getting involved in social freedoms I should not be considering getting “actual” married. Sure, a small ceremony would be nice, but the legal side of it frightens me quite a bit — especially since so many people I know who are older are divorced and worse off for it.

While I don’t at all expect to get divorced ever (hey, we’ve made it almost nine years as bf/gf and if we do get married it will be on our 10 year anniversary – by then I think I’d know what I’m getting into) I still don’t know if marriage is a good idea, financially speaking. The way marriage is set up… and the tax laws around marriage… is that you are rewarded for having one working parent and one stay-at-home parent. If you have two working parents and earn reasonable salaries you actually can have what they call the marriage tax penalty. Before tying the knot, I really want to better understand if that is going to cause a fiscal knot in my future bank account.

After writing this post, I found this awesome breakdown by Financial Samurai which details out the tax benefits or penalties for different types of married couples — it is a must read!

How Marriage and Tax Works

Starting the year you get wed you are officially a married couple in the eyes of the government — even if that happens on the last day of that year. You have a choice now to file married jointly or married separately. If you and your partner both work and make equal salaries, unless you’re low earners like teachers or social workers, you’re going to probably be better off filing separately.

The problem is — married filing separately doesn’t actually mean the same thing as filing as a single person. If you file separately while married you cannot take deductions for tuition fees, student loans, social security benefits tax-free exclusions, credits for the elderly and disabled, earned income credit, hope or lifetime learning education credits, child care credits, etc. And if you decide to file separately and one partner wants to itemize, the other partner needs to itemize their taxes too, even if they have no reason to do so.

But the bigger issue is for higher income earning couples. As you can see below, married filing separately and single filers do not have the same tax brackets. If you are married filing separately, anything over $74.4k will be taxed at 28%, where if you are filing single you have until $89.3k before you are bumped into the 28% tax bracket. If you happen to earn more than $180k per year as a ginle person you’ll still be within the 28% tax bracket, but if you’re married filing separately you’re going to pay 33% for any income over $113.4k.

Of course if one parent works and the other doesn’t the tax table works in that couple’s favor. I.e. say I work and make $200,000 per year and my husband stays at home and makes sure that the kids eat and don’t die — filing jointly we could remain in the 28% tax bracket, whereas if I were filing single and not married my top income would be in the 33% federal bracket.

2014 Tax Brackets (for taxes due April 15, 2015)

Tax rate Single filers Married filing jointly or qualifying widow/widower Married filing separately Head of household
10% Up to $9,075 Up to $18,150 Up to $9,075 Up to $12,950
15% $9,076 to $36,900 $18,151 to $73,800 $9,076 to $36,900 $12,951 to $49,400
25% $36,901 to $89,350 $73,801 to $148,850 $36,901 to $74,425 $49,401 to $127,550
28% $89,351 to $186,350 $148,851 to $226,850 $74,426 to $113,425 $127,551 to $206,600
33% $186,351 to $405,100 $226,851 to $405,100 $113,426 to $202,550 $206,601 to $405,100
35% $405,101 to $406,750 $405,101 to $457,600 $202,551 to $228,800 $405,101 to $432,200
39.6% $406,751 or more $457,601 or more $228,801 or more $432,201 or more

This all seems like marriage isn’t the best idea unless I plan on remaining unemployed and being a gold digger the rest of my life. It’s hard to know what the future holds, but the reality is that marriage might not be the best idea financially speaking. In fact, if I get married it will be likely that my husband and I will each earn around $130k AGI each, or more. If we earn $260k jointly we are in the 33% tax bracket. If we each earn $130k and file separately we are also in the 33% tax bracket for every dollar earned over $113k. BUT if we weren’t married at all and earned $130k all of our income would be in the 28% tax bracket.

Am I missing something here, or is marriage just a big scam to get us to pay the government more of our hard-earned money?

This article seems to make the case that marriage isn’t worth it – unless you plan to have only one working partner or both be very low income earners.

Some Other Items to Note

  • BONUS: You can get joint health insurance if one partner has it through work… this isn’t a tax benefit but it is a benefit to being married.
  • PENALTY: The Child Tax Credit provides up to $1000 for every child under 17 in one’s care, but if you file a joint return the credit phases out at $110k income total for both partners. If you file separately you don’t get the credit at all. If you are not married and file single it phases out at $75k (**again a reason why this should be determined based on cost of living because $75k is a large salary in some areas of the country and in others it’s not enough to afford a basic lifestyle.)
  • PENALTY: Miscellaneous deductions can lower taxable income, but they need to add up to more than 2% of AGI to actually matter. If one spouse has these deductions but the other doesn’t, it can be a big headache since both spouses have to itemize if one does. That also can cost more to prepare since it’s no longer standard TurboTax click click and done.
  • BONUS: If you’re married and own a home with your partner, you can take $500k in gains tax free when you sell for your next house. If you’re single you only get to take $250k in gains. That said — most of us won’t have more than $250k gains on a property because we’re buying houses that at most are $1-$1.5M. Aimirite?
  • PENALTY: Obamacare requires an additional 3.8% tax on net investment income when gross income exceeds $200,000 at a single tax payer… BUT $250k as a married couple. So basically if you earn $125k each (totally normal in cities like San Francisco or New York) you are going to pay a lot more on your investment income. Being single and making under $200k is a lot more reasonable.
  • BONUS: If you are married you can give each other as much money as your heart pleases because you basically now are the same person. If you happen to die unexpectedly, god forbid, your partner can get all your monies tax free. This is the one true bonus of marraige left but does it outweigh the extra taxes paid annually as a married couple? (Otherwise I’d think you could just get married later in life once you are ready to take advantage of tax-free cash sharing.)
  • PENALTY: This also provides a strong incentive for your partner to hire an assassin to make you disappear, if you happen to be the keeper of said monies (or maybe I’ve just been watching one too many episodes of law & order)
  • PENALTY: To deduct unreimbursed medical expenses they must be more than 7.5% of your AGI. If one partner has a big surgery that costs a lot and cannot work during the year — and is single or filing separately — he can take that deduction. But if the couple files jointly and the other partner makes a lot more then the deduction is harder to obtain.
  • PENALTY: If you make more money, more of your Social Security is subject to tax. You’re better off filing single vs married to keep more of your SS benefits. Also if you are a couple with two working partners — you’ll end up with more social security in the long run if you remain single!
  • PENALTY: The AMT (Alternate Minimum Tax) exclusion for two unmarried individuals is much lower than that for a married couple, and this can cause upper middle class earners thousands of dollars in extra tax each year.
  • PENALTY: If one partner earns less money in one year than another, if the couple remains single filers one person who earned more money can gift the other up to $13k in appreciated stock, tax free, which she could sell at her capital gains tax rate (which could be 0% if she is not earning anything that year, but filing jointly at that point might actually save the couple more.)
  • PENALTY: A single person can deduct up to $3,000 in capital losses per year. Married couples… can only deduct up to $3k in capital losses (not $6k.)
  • PENALTY: If a couple is unmarried and, say, the woman owns a house in her name and the man gets sick and relies on Medicaid to pay for a nursing home, Medicaid cannot come after the house that the woman owns. However if they are married they can take the house away!
  • PENALTY: The Roth IRA contribution limit for a married couple is lower than it is for two single individuals! If you’re a single person you can invest $5500 per year in a Roth IRA if you earn less than $114k per year (AGI) — BUT — if you’re married, you can only earn $181,000 jointly to invest in a Roth. That’s $47,000 less income you can earn and still be eligible to invest in a post-tax IRA account.
  • PENALTY: Write-offs from rental real estate can be used to offset ordinary income unless your AGI exceeds $150,000. That is — $150k as a single person or married — that amount is the same!