Tag Archives: job

Should I stay or should I go?

I was depressed about my job and decided it couldn’t hurt to start applying to roles that really struck my eye, full well knowing that historically I’d apply to hundreds of positions before getting a few calls… and it would take weeks to hear back, if I ever did.

My plan was to stay at my current job at least until the end of December, so I could finish out my year and really wrap up the current projects I’m working on so hopefully all involved could look at my time at the company as a success where I clearly added value, even if it was time to move on. I figured starting to apply for jobs now meant I’d maybe have a few interviews starting in late September/early October, being drawn out through October, with the earliest I’d get an offer being late October/early November. With a little negotiating I could bump out my start date until sometime in December. Continue reading

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The High Cost of Mental Illness

Mental Illness is a touchy subject –  unlike, say, cancer or diabetes, it isn’t something that can be diagnosed via blood tests or biopsies. And everyone suffers some amount of anxiety and depression at different times in their lives. I’ve struggled with my own mental illness for years, both being tortured by its overwhelming nature, and, often in the same day, telling myself that I’m overreacting and totally fine.

Mental health conditions cost employers more than $100 billion and 217 million lost workdays each year. When I’m lost in a web of anxiety, I know I’m not being a good employee. This reminder of my failure as an employee spins me into a deep cycle of depression and worthlessness which quickly spirals out of control. I get so mad at myself because I simultaneously feel like the greatest impostor of all time and know I can do a better job that what I do right now, but the sadness of being an obvious fraud gets in the way of productivity. Eventually, my boss catches on, and I move on. I put so much of my personal worth on my job, I really don’t have much else in my life outside of my job and my husband. My career is everything. Maybe that’s the problem. Continue reading

Why Do I / Do I / Even Want / This

A wise friend of mine the other day raised a very interesting point – why do I want to be in a senior leadership role? It first struck me as a strange questions – who wouldn’t want to be in a senior leadership role? Isn’t that the point of working – to be able to strategize and lead a team to achieve substantial goals? It doesn’t have to happen now but it is the eventual goal if you want to move up in your career.

He shocked some sense into me by noting that he doesn’t know many people – if any – that really WANT to be in such a senior role. No one wants this role because quite frankly it’s impossible to succeed in it… and I do feel it’s even harder as a woman (especially a socially awkward one) than it would be for a man.

The best senior leaders don’t actually do any work. They successfully hire / fire right and motivate their team to be their best aligned to the company’s common goals and they promote the shit out of themselves and their teams without sounding like their boasting. That’s it. That’s why successful executives tend to be the people who have a BA in BS – it’s a very valuable skill/trait to have, and it’s something so alien to my being that I am now convinced I ought to give up.

It is very clear that my current company is seeking to replace me as soon thats feasibly possible. I found out, through various means, that they’re interviewing for someone more polished and been-there, done-that to take over without actually telling me as much. It appears one candidate was far along in the process and took another offer, so perhaps this buys me some time. But I don’t want to buy time. I want to be good at my job. And this is the type of job I’ll never be good at. Why? Because I do too much.

I hate playing the gender card but I do think it’s a lot harder for women to get away with just being leaders. In a small company no one can really just manage – yet the true leaders are the ones that bring value to the table in their public speaking abilities and relationships, and everyone else does the work, work. Except – when you’re a female executive, especially a young, unproven one, you have to be both a leader and individual contributor. What I’m learning is most men wouldn’t even take a job that requires them to do that. I just seem to be a professional masochist.

That said, I’ve been going back to why I wanted this or any job like this in the first place… and the moments when I truly love what I do. I don’t really care about being the head of anything… but I do like to be in charge of strategy and lesser so execution. I’ve never done well working for someone who tells me exactly what to do. I have ideas and quite frankly I believe many of my ideas are good ideas… though my execution is admittedly lacking which gets me back to, well, this damned place where I know I’m on my way out, whether I like it or not.

My very german therapist tells me I need to stop chasing money. So do my blog readers. But it isn’t the money that makes this a job I like. I enjoy the wins. I am fueled by the victories where I can clearly show my contributions helped the bottom line. Perhaps I’m delusional in how much influence I can actually have given my anxiety drives my mind in unproductive circles time and again around the moments when I actually get shit done and put a dent in the everlasting pile of work that isn’t clearly defined yet is sitting so glob-like on my already-cracked and seemingly soon-to-be shattered plate.

But… I guess it’s true… not many people want to be in charge of departments. Especially not many people in their early 30s. That’s something you do when you’re 50+ and have many years of experience under your belt and the lines in your face which organically garners respect. The only reason someone like me gets hired in a position like this is 1) at the time I’m hired, better people for the position aren’t interested yet in joining and 2) better people for the position would refuse to join unless they were set up for success which = larger team so they don’t end up having to do all/most of the work in order to claim success.

Now, don’t get me wrong here – I’m not complaining about having to do work. I’m just struggling with being a senior executive and junior-level individual contributor and mid-level manager and creative expert all at the same time. This is a requirement of this role not in my company specifically but any small company hiring for the position, with slight variations. You are tasked with being everything and yet when you fail to do that you’ve let the world down and clearly you were a bad hire. Then the company goes back to the drawing board to learn from it’s “mistakes” and perhaps hires someone more traditional who can go through the motions at the least in a way that’s much more convincing than I ever could. In the end, though, few succeed. The best execs I know have all left startups. They’ve figured out that their best chance of success is to use their charisma to manage large teams and be that rock which inspires the masses to get shit done and not let said shit hit the fan.

I’m not that person. I’ll never have consistent, readily available charisma.

I can’t fake it. I drain too easily. I need to hide in a corner for a day and recharge.

My friend noted that if you want to become a senior exec you don’t try to become one, it just happens when you’re good at something. He’s right. I never was able to get good enough at any one thing so this whole career progression has been forced and riddled with improbable success paths and far more roads to failure. That’s just where I’m at now. It’s a lot to think about… but at least I feel myself pulling closer to accepting that I’m not a senior exec, I shouldn’t be one and I shouldn’t want to be one. So what should I want to be?

When You Made It and You Haven’t Gotten Anywhere

This week, I’ve been reading a slew of posts about how women make less money than men, and why.  Mostly, the argument against this being an issue goes, that women tend to work less than men one they have kids, and they also and generally less competitive so of course they don’t make as much money. In every single job negotiation I feel the weight of this on my shoulder, and try my best to negotiate. I have no idea what a man would do in the same situation with my experience, but since my first couple of jobs when I took the starting salary with no negotiation at all, I’ve tried to ask for a little more, and I’ve gotten more ballsy over time. It helps now that I now have competition offers, and I seem to be fairly good at interviewing these days.

On paper, I sound qualified for a very particular type of role and particular type of company. I’m not sure at all how life has sculpted itself to this specific career path, but it has, and I’m locked and loaded into it, full speed ahead until retirement to gain more responsibility, earn more wages, and look back on a very successful professional career. It hit me this week that I’m nearly making $200k (which, even for one of the highest cost of living areas, is one of those numbers that I thought would never be possible — ten years ago I was making $20k.)

Yet as I look ahead to potentially having children / starting a family, I realize that if I have an opportunity to leave this profession and move into something that is more flexible and personally fulfilling, I would. As much as I like money, and as much as I’ve been driven by this random “$500k in networth before I have kids” goal for the entirety of my 20s and early 30s, I just can’t see myself, 10 years from now, in this same type of role. I don’t want to be a vice president or C-level executive. Even though the pay would be great, I have no desire to be that person. I could potentially figure out how to fake who I am enough to get there… given my success getting this far, I have to believe that someone out there would want to offer me such an opportunity one day.  And I feel very guilty, that as a woman — as a woman who has an actual chance of getting to the top – I don’t want it.

As I sprint full speed ahead towards my mid 30s and the next phase of my life, I wonder what to do about it. I’m so busy these days with just trying to do my job and do it well and planning my wedding that I don’t have a ton of time to ponder what’s next (which is probably a good thing.) But, as my rent has increased this year by $2040 for the year, and the cost of living in this area shows no signs of refraining its hockey-stick growth, I know that at some point soon, I either need to commit to this career or come up with an exit strategy. I’m leaning towards the exit.

I don’t want to “not work.” I LOVE working. I love collaborating with a team to create new products. I wish I could be a ux designer or product lead. I’ve said that now for 12 years. I’ve failed to make any progress in that direction. I tried to study for the GRE and even booked a test slot and then didn’t go because I hadn’t studied enough. I couldn’t focus. I gave up. I got a better job. I made more money. It became less fiscally responsible to go back to school anyway. I got older. I passed that age when people go to grad school into the age when some people do but they’re much older their classmates. I entered the age where you take online classes or executive programs but only in rare cases do you go back to school for an entirely new career. Sure, people do it, and I may eventually as well, but I’m really getting older now — not old, per se, but old in the sense of I have a career. I have a good career. I manage a department, small as it is, I’m still in a high-level role, and there is so much good in my life that I kick myself every time I want to start over.

At this point, I’m committed to another year or two in my current job. If I do get pregnant then that will certainly be an opportunity to think through what’s next. Of course, if I get pregnant, it will be even harder to change careers. If I opt to apply to grad school for 2017 I’ll be 33 when I start, and I may want to put having kids on hold, which means I likely won’t have kids, which is, at this point, out of the question unless nature says I can’t (also a possibility.) In any case, there has to be some major changes in the next 2-3 years of my life, which will likely include moving to another state, or at the least, finding another career path and opting for lower pay and a lower quality of life here. I know this isn’t something I can maintain. It will be hard to say goodbye to the near-$200k salary, but I know if I figure out how to do something I’m really passionate about, maybe I can get back there over time. Or maybe I can just make less money and live somewhere more affordable. Either way, there are options, and I’ll always feel guilty as a woman for throwing away a successful career, but I have to. I have to rethink my entire life, my goals, and the directed outcomes. I do finally feel ready for a change.

Waking Up from The American Dream

Today, we received notice for our annual lease renewal. Our rent will be increasing $170 a month to a total steal of $2465 for a one bedroom apartment, not including any utilities. If we lived in the city the same apartment would be at least $1000 more. That’s life in the most expensive area in the country — no matter how much you make, you’re still not making enough to afford the life you thought you’d have at this point. You just have to wake up from the American Dream and realize it’s just that – a dream.

I’m incredibly fortunate to be one of the few who is making a high salary — more than I could ever had imagined making and more than I believe I deserve. At the same time, I acknowledge that in order to afford a house here you pretty much need to be taking home $400k (as a couple) which isn’t in the cards for our future, despite my relatively very high income – even if I manage to find success and stability in my job. I realize that many others will never even make as much as I do, and I feel I make too much, but it’s a loop of relativity when I try to comprehend how much I’d really need to make in order to purchase a 3 bedroom house with a tiny backyard.

Do I need a 3 bedroom house with a tiny backyard? Even if I don’t, soon our rent, for a one bedroom apartment, will creep up to $3000 a month, even in the suburbs. We won’t exactly be priced out but we’ll be able to save less and less each year. At some point, I think we’ll have to accept that it’s time to leave. And with a total income of about $250k, we’re doing much better off than a lot of people who live here. It’s just not enough and it will only get worse as we attempt to start our lives together.

If kids end up not in the cards, maybe it’s doable. We can stay in a one bedroom apartment, no need to pay for extra space when it’s just us. We can live in a one bedroom for the rest of our lives. This isn’t at all the life I had imagined, but we can survive easily without that much space. If we do have children that changes the story quite a bit. I don’t see how we can have children and remain here, especially if I need to take time off for any reason. The pressure of being the breadwinner, especially suffering from severe anxiety, is too much. If I am responsible for me, myself and I — that’s no big deal, I can roll with the punches, live cheaply when needed, and just weather any storm that comes my way. With children, we need a much bigger security net. We’ll have to move. We will have no choice.

I write this at a time when many entry-level workers here are seriously struggling, unable to feed themselves or pay rent on minimum wage. I feel embarrassed to look at my quite high income and still feel so hopeless, because if I feel hopeless, how on earth is the rest of everyone supposed to feel?

I’ve come to accept that if I’m going to have children we can’t stay here. I don’t have a solution yet or an answer to “where to do we go,” but sooner than later we have to get out. I’ll very much miss the beautiful scenery and sunshine. I’ll look back on my 20s and be glad I had the opportunity to live in such a glorious part of the world. But it’s time to grow up and move out. Or, at least it will be soon.

People say to not worry about the future and to just live in the moment. I find it very hard to do that. We now face the choice of staying in our current apartment and paying an extra $2000 to do so next year (and continuing my 3 hour a day commute) or finding a place closer to work that will either be more expensive or less livable or both. We’ll probably just stay here for another year – neither of us wants to deal with moving, and $2000 doesn’t seem like that much compared with the inconvenience of finding a new apartment and lugging our stuff to it… moving isn’t free either. So we’ll probably give it on more year here and hopefully by the end of the next lease I’ll be pregnant and we can then figure out where on earth we’re going to live in the future (aka not California.)

I had hoped that I’d be at a point in my career where I’d feel so distraught over losing my job / career in order to have a family… but while I appreciate my job for what it is now, and really admire my colleagues and am so grateful for this opportunity… I have no personal investment in this career. I feel no sense of pride in my progress or role. In five years, to continue on this path, I end up in a leadership role were I will never fit. I acknowledge it’s soon time to leave. Right now, the best I can do is hold on for dear life, do the best I can, and try to save money by living relatively frugally and bringing in a good income where most of it goes straight into the stock market / my savings accounts. This may be my last significant savings opportunity in my life, given I plan to move to an area with a lower cost of living and obtain a job which pays significantly less in my next career move. My goal is still to get to $500k in savings before I make this move, and the goal is becoming much more dire given that I’m rounding the corner of my mid 30s and I know I can’t handle this life for much longer. If I can just hold out until $500k — I can completely shift my lifestyle to one of lower income and greater flexibility in another part of the country. We can live off of, say, $100k total across both of our incomes and still live a decent life. If we make more than that, great, but we don’t have to (or, in the case of staying here, I’d likely have to earn over $300k in order for us to hit the $400k mark and afford a small home.)

What was once kind of this running silent joke in my head about how one day I couldn’t afford to live here and that I’d move away is proving true. I guess what has changed is that I’m more ok with that than I was before. I used to think that I didn’t want to trade my career for a simpler life. I didn’t want to be one of those women who had kids and no longer had her own identity, especially a professional identity. But now, I don’t know, my professional identity is not who I am. Despite not making it to Hollywood or Broadway I’m an actress nonetheless, everyday portraying someone who I’ll never be. I’m over this obsession with what I thought was success. I have nothing to prove, no one to impress, no game to win. I have maybe 60 good years left on this earth if I’m lucky, and many fewer with all of my loved ones in good health. I hope to make the most of them, and it doesn’t matter if that occurs within a tiny apartment or a giant house. It feels good to finally accept that… to embrace the loss of this embedded classism my parents have taught me, to stop feeling like if I can’t maintain the level of comfort and luxury from my childhood that I am a failure. The only true way to fail is to lock myself into a life where I no longer have any reasonable options for escape.

Mozart in the Management Jungle

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After a weekend of binge watching Amazon’s Golden Globe-winning Mozart in the Jungle, I felt equal parts saddened and inspired. Saddened, because the show follows the lives of artists — musicians — who dedicate their lives to creating. Their madness is enhanced for comedic purposes, yet the madness of a musician is something I mentally relate to far more than that of a CEO. However, I also found the show offering lessons in leadership, and a reminder that the conductor, while expected to be versed in numerous instruments and able to step in to play if needed, is considered successful as a leader, a director, an – orchestrator – not a musician, i.e., an individual contributor.

I’ve always wondered why conductors were considered so important — all they do, it seems, is wave a stick and keep everyone playing at the same pace. Perhaps they would make a bigger motion to increase volume, but it seems to be largely for dramatic effect. What does the conductor actually do? Why do orchestras — filled with musicians who can read music as well as most of us can read the English language — need a conductor to begin with?

My challenge as a manager is stepping away from my nature to be an individual contributor. Although in a small company, I cannot walk away from the individual contributor role entirely, my value is in being the conductor. With this in mind, I return to examining the value of a conductor – not as someone just waving a stick in the air in a marvelous rhythmic dance, but someone who is leading a team, interpreting the “best practices” of the music and adjusting with their vision, keeping everyone together, guiding them through to the final product. The conductor’s work and value, I’ve been reminded, largely is contributed before the product release (aka the performance.)

I think I’m actually a very good manager as a conductor, but when I’m trying to play the proverbial violin and trumpet and oboe at the same time, it makes it nearly impossible to conduct successfully. Although the conductor may step in to fill missing seats, it’s her responsibility to hire the right musicians and then inspire them to follow their greater vision. A manager must do the same thing. She must hire the right team members and determine what role they should play, how loud they should play it, and otherwise orchestrate the score of any given quarter’s objectives.

While business isn’t art, it’s still an orchestra of creation, and still needs to be conducted. Without a conductor in an orchestra, perhaps experienced musicians could play music – but they wouldn’t know which music to play, or how fast to play it, or what to do should one of their violinists get sick for an extended period of time. In romanticizing the life of an artist – which I do frequently – I find myself feeling most alive when I approach my own work as practical art. I can still bring the passion which a conductor brings to the stage in front of a large concert hall during a sold-out performance. I can inspire people to be excited to play their instruments from start to finish, even if they’ve played this score a million times. I can inspire them to think differently about the music, to hear subtle shifts in rhythm and composition, to try new things, take risks, and ultimately learn and grow and make the great music of increasing ARR.

In orchestrating a team, there is a musicality to the work, a rhythm which must be established, an ecosystem of players who must all come together to accomplish a common set of goals. So, while I likely lost the chance to live the life of the broke artist, I’ve gained the opportunity to make a new kind of music – one that 10 years ago I didn’t know existed. When I feel overwhelmed or frustrated or scared, I now close my eyes and imagine myself with a baton in front of an orchestra, and I examine by players as well as the notes written on the page, and with a deep breath, I lift the baton, and my team begins to play.

Hello 2016! A Toast to an Amazing, Productive, Healthy, and Sane Year

I’ll admit it, 2015 was rough. With my long commute to and from work, my sanity and health sank to perhaps an all-time low. Although I achieved networth growth over the year, it wasn’t nearly as much as I had targeted. In fact, in the year when I made significantly more than I had ever made before, I ended up saving less than I had in the past (including interest.) I closed out the year with $344k in total assets with the exception of my car (I don’t count that in my networth calculations, though, I guess I suppose I should.) I wanted to be at $400k in networth, but between some bad investments, general stock market blahs, and being unemployed for a brief while, I just didn’t get anywhere near that.

What I try to remind myself is that $344k at 32 is not too shabby. If I don’t touch that, don’t add anything else, and it manages to grow at 5% YoY that’s $1.3M by the time I’m 60. Ok, so I want to get to $4M by 60 (which requires about a 10% YoY annual return with my current principal and no annual additions), but even if I get to $1.3M by 60 I think I could remain working and manage to grow that another 5  years, which gets me to $1.7M and that isn’t counting any savings from future Mr. HECC.

The plan was to hit $500k net worth, have a kid and save for a house while living in an apartment with young kid, and then over the next five years save enough for a 20% downpayment ($300k) on top of the $500k plus annual interest that I wouldn’t touch. That goal is looking rather unlikely right now, and I’m actually ok with that. I’ve gotten to this point where I’ve accepted that the life I am going to lead as an adult is going to be at a lower class level than the one I was used to as a child. While I grew up in an upper-middle class household, my family will be squarely in the middle class (for my region of the country), and we’ll be fine. We’ll still be doing much better than the majority of households in the country, even if we can’t afford a house for a long time, if ever.

Right now, my focus must be 100% on excelling in my job. With my current salary and responsibilities, I have the opportunity to set myself up for a very successful next 20 years of my career. I also am very seriously confronting the reality that if this doesn’t work out for any reason, if this is a failure, then it means a significant shift my career trajectory and networth projections. I very well might return to school – which I’ve been talking bout for a while but haven’t seriously pursued – to study to become a psychologist or design researcher with a psychological focus. But I don’t want to think about that right now, I’m heads down, fully in the game, trying to relax and thrive despite the many challenges at hand. In other words, I refuse to mess this up.

Beyond work, this year is just a huge year of major life changes. I get married in a few months (tax bill goes up next year, woohoo), and I also likely start trying to have kids, confronting the soon-to-be-proven fact that conceiving doesn’t come so naturally to me (thanks PCOS.) I’m hyper-focused on losing weight, eating healthy and exercise right now. My weight fluctuates significantly — in 2012 I was at 180lbs (my highest ever, which is very heavy for a woman who is 5’3), to 155lbs a year later, to 176lbs a year later than that, dropping and holding steady at 170 through 2014 and most of 2015, ending 2015 at 160lbs. I hired a personal trainer 3x a week ($50 a session which is a really good deal for this area) so we’re working on getting my weight down to about 130 in the next couple of months (5 pounds a month is my goal to lose, which is a good, achievable goal.) It’s mostly so I can feel happy with how I look in my wedding pictures, but it’s also just something I need to do in order to save myself from premature aging. Plus, I just feel mentally more clear and balanced when I’m eating healthy and exercising. It’s good to have such short-term goal so I am focused the entire way through, no matter how hard it gets.

This year, my goals are going to be a little less intense on the networth side. I’d like to get to $400k in networth, including $23.5k in new retirement savings (401k & IRA). That leaves $31.5k to make up for in interest and other savings, or about $2.6k per month. I’m planning to try to save an additional $2k per month on average, and hopefully the rest (~$7200) will come from interest on, say, $250k of invested, interest-earning assets, which is about a 3% gain on those investments. I’d prefer to go well over this, but trying to be realistic with the goals, especially with the wedding spending. I don’t think this is going to be a hugely profitable year but I could be wrong.

2016 Goal Summary

1) $400k networth – including $23.5k in retirement savings, $24k in taxable investments, and about $7k in interest.
2) Be 130lbs by summer
3) Thrive at my job (and be gainfully employed and loved by my colleagues when Jan 1, 2017 rolls around)
4) Get pregnant before I’m 33!?!

Well, here’s to kicking off what is sure to be a crazy year. Fingers crossed it’s a good one. I think it will be. I hope it will be. Oh god, it better be. 🙂

 

 

 

The Gender Pay Gap from the Top and What to Do About It

Last week, Salesforce CEO Marc Benioff announced that the company paid $3 Million dollars to correct gender pay imbalances across its organization. Although this isn’t a huge number for a company of it’s size, it’s still telling that the firm found $3M in imbalances to fix in the first place. This means that when they ran the numbers they believed that women were earning less than men in the organization for roles of a similar level, and they decided to publicly fix this. But why was that the case in the first place?

As I approach my job negotiations for a senior-level position, and I’m incredibly uncomfortable with doing so, I remind myself that I have to negotiate because any male in my position would. As one woman, I’m not representative of all women, but I can say I find it incredibly hard to negotiate. As a woman, I may read negotiation advice and bring a request to the table based on research from online websites that give some idea of pay ranges. And, as a woman who doesn’t like to shake the boat, I’d typically pick the average to ask for because it feels uncomfortable to ask for anything more.

But I’m not an average woman, and I try to push myself to ASK. This gets harder and harder as the numbers get bigger. I always like to state that it is a PRIVILEGE to have this problem, but it is an issue nonetheless. According to this Harvard Business Review article, the Gender Pay Gap Widens as Women Get Promoted. Basically, the higher up in the organization a woman is, she is likely earning less than her male counterparts. A female executive earns 6.1% less than a male, compared to only a 2.2% gap in an individual contributor role.

The problem with negotiating as a woman is that you can’t win. There is plenty of research that shows women pay a higher social cost for negotiating. I’ve experienced this first hand. In my last role, I negotiated very well (in my opinion) but the I was reminded pretty much every single day from my boss that I was making “so much money” and this made me insecure and ultimately defeat myself in the role. I would have been more comfortable had I been earning less and not rocked the boat.

But what I come back to is this – my role is one that generates clear revenue for the business (well, if it doesn’t, I don’t get to stay for all that long.) I’m working for a for-profit organization in a revenue-generating role, and I deserve to be paid for it. Even then, I have no way to know if I’m overstepping — a man in a senior role can ask for anything. He may not get it, but it’s accepted that he’ll ask. A woman in a senior role worries she’ll offend someone. That’s just how it works.

The HBR article notes that while it’s not clear why female executives are paid less than men, it appears that women need sponsors in organizations more than they do mentors. My strategy has been to change jobs relatively frequently in order to move up and earn more. I would not feel comfortable negotiating for higher pay once I’m on a successful track within an organization. It’s at least a little easier to negotiate at the start — but the big question is, how often do men negotiate throughout the year when women do not? Do men ask for bigger raises each year, or do they request salary increases at a more regular frequency than women? Are the raises of similar frequency but just more substantial due to executive sponsors? These are questions no one seems to have a good answer for, so we’re all left in the dark.

In order to solve this problem, organizations need to be provided training from the top down and bottom up about negotiating. It’s tough to do this because it’s in the best interest of the organization to pay each employee as little as possible to keep them engaged and working as hard as they can. If one employee will accept less than another, this is good for the business, at least on paper. And if no one knows how much everyone else i making, how much can it hurt? But wouldn’t it be crazy if a business actually taught people how to negotiate and encouraged it, making typical negotiation timelines around promotions (official and non-official) more transparent? I wonder if anyone would do that. What Salesforce did is a good first step – but also a good PR move. How long will it be before those salaries are unequal again? And what can we do to fix that?

To start, I’m always going to ask for more, even when it makes me sick to my stomach, and even when I know that my likability factor is dinged, because in the long run to be successful, if you’re a woman, you can’t be liked. You can only be respected.

 

 

 

The Jobs. The Offers. The Decisions. The Lack There Of.

It used to be getting a job offer was a huge challenge. It’s not exactly easy today, but I find myself in a place where I have three serious offers (well two offers and one offer if I wanted it) and I’m trying to figure out what to do.

Both offers at this point are somewhat equal in terms of compensation. Base salary is identical in the initial offers for both. One has a bit more stock, the other, a bit more bonus / cash earning opportunity. I haven’t accepted any so theoretically there is room for negotiation. I hate negotiation. Last time I negotiated I got the salary I wanted but then I was reminded over and over again by my boss how overpaid I was (btw, I wasn’t, given the offers I’m getting now are even more than what I was paid there, so clearly market rate wise I was fairly comped in my last role.)

The reason I hate negotiation is that I have no one at my level in a comparable role to talk to about it. At this level of compensation and given my relatively frugal lifestyle, even for this area – on one hand, when numbers get this big, I feel just downright silly negotiating for more money. On the other hand, I think – if I were a dude or someone with confidence, I’d negotiate anyway. Ultimately, my role in either firm is one that indirectly generates revenue for the business – it’s pretty cut and dry if I have generated revenue or not (granted, I’m not closing business, but I’m still generating it) and thus I think a bonus compensation structure makes sense, and that structure should be more or less unlimited as a percentage of sales, or at least substantial in a tiered structure where maybe base stays about the same but total compensation is based on how well I do my job. If I do my job well – then I’m “cheap” – if i’m not, then I’m – “gone.” Low risk to the company either way, given they plan to hire me (or anyone else for this role.)

But I hate that awful taste of negotiating for more – and ultimately I want to pick the job where I can do THE BEST job. And I don’t know which that is right now. I’m not at the point in my career where I can get an offer at a company that has its shit together. That means either I get an offer at a new, young company where it’s still figuring things out, and where it needs someone who can deal with the ups and downs of startup life — OR I get an offer at a company where things are probably more systemically dysfunctional due to years of poor management decisions, but one that has managed to sell enough of its product/service to still be alive either private or public, it doesn’t matter as both come with their own challenges.

I seem to be a perfect fit for those environments, maybe thanks to a very turbulent childhood. But I also think a positive, healthy, rather successful work environment would be nice. My challenge is that I’m not so great at maintaining the status quo. I’m someone who comes in and creatively solves problems. I fix things or build things but I certainly don’t inherent the same old and run with it as such to collect a paycheck. I like moving fast and getting in and making a difference. But then, as history has proven, either I do that really well for short bursts or I can’t manage to figure out how to fix things fast enough and I’m out.

My last job was a trainwreck from the start. CEO who sexually harassed (in a joking way, but nonetheless, it was sexual harassment) most of the women in the company and heck, even some of the men if you were to ask a real HR department. I learned a lot in the role but there were just so many things wrong with the company that I felt lost at what to do. Too many things to fix. Too many holes to fill as water would start leaking out another opening I didn’t even see.

If I go to the smaller company, my main priority will be to hire a small handful of really great people really fast. Hiring is hard. People have to want to work with you and the rest of the team. You (me) have to be a leader. A true leader. In my mind I like to think I’m a leader but what I see in leaders I admire I don’t see in myself. They are very strong, determined, and once they pick a route they don’t chance course (and if they do it certainly doesn’t appear they did this because they realized they made a bad decision.) Leaders have a very clear vision and get everyone aligned to common goals. I have a hard time getting myself aligned to a common goal, let alone a team.

The larger company would immediately have me managing a decent-sized team. It’s a huge opportunity in that if I can successfully manage a team and help them become more productive, that’s a metric I can take to the bank for the rest of my life. I can also build a team at the smaller company and have a similar outcome, but at the second company I would’t have to hire immediately. I’d have something to work with. That can be good or bad, depending on the contributions of the team today and what I figure out needs to be done to hit goals. It likely involves being able to come in and, if anyone isn’t holding their weight, being that bad guy and letting people go early on and replacing them. You know – typical management stuff that I don’t like to do because I’m an INFP and I can’t handle hurting people’s feelings, only letting them down.

I still am most excited by the smaller company… if the larger one was a bit more stable, or selling a product that I could get extremely excited about, it would be a different story. But I have some good opportunities here and I just need to finalize what I’m going to do… it’s a good problem to have, for sure. I just am at that point where I really don’t want to make the wrong decision… and I’m not sure there’s a right one to make. Because – when it comes down to it, I’m in the wrong career overall – but it’s a hot market and people keep throwing money at me and it’s hard to say no. It’s easy to say – one more go, let’s see if I can make it happen… I’ll try my absolute best… and in the meantime, keep on putting away $5k a month to attempt to reach my goal of $500k in networth before I give birth to my first child. After that, I feel like I have a bit more flexibility/freedom to maybe switch jobs and earn less, or consult part-time at a higher hourly rate, or… anything other that continuing on this trajectory which can’t be forever.

 

The Reality of My Professional Apptitude

As I review my next steps, I have many, many, many variables to consider. Above all, I want to take on a role where I can be successful *long term,* not just for a few “burn myself out” projects — OR, take on a role where “burn yourself out” projects are the norm. I’d be much better off in a creative industry working on television shows or movies, but it’s a bit too late for that, especially given my massive fear of change. I’m trying to work with what I’ve got here. And, at the least, I have options. And good ones at that.

Ten years ago at about this time, I was getting fired from a marketing internship at a non-profit. It was my first year out of college and I didn’t know what on earth the future held or what I wanted to do. I applied for hundreds if not thousands of jobs and rejection emails gave me a warm, fuzzy feeling that someone or something out there reviewed my experience, or lack thereof, and decided to personally not give me a chance. Since the full-time job thing wasn’t working, I applied to a pretty-much unpaid reporting internship and, when I found a place to live, found a part-time admin job which was never a good fit for my ADHD self. I survived the entirety of the internship, but the part-time admin gig was, well, a predictable disaster.

Although I moved on and continued to apply for job after job after job, I didn’t know what I wanted in life. I had no friends in the area, very little family, and the only reason to live was to try to make money… to save a little bit… to build something when everything around me was crumbling. I somehow impressed a magazine that I was a worthwhile hire for an editorial assistant role and I stayed for a year, writing articles and attempting to become a better reporter. But my social anxiety really got in the way of that. I did the blogger thing for a short while, which was even worse, because bloggers need to be super aggressive and not let anxiety get in the way of getting a scoop. My journalism career practically ended before it started.

Without rehashing my C.V. for the thousandth time, the point is that I haven’t really massively succeeded in any one role. There have been pieces of roles where people have seen my strengths, and there have been times in the past 10 years where I’ve really poured my heart and soul into projects, and they’ve been considered significant successes. But nothing has ever been sustainable – you can say I just need to suck it up and work, but when you have ADHD and bipolar disorder, it’s not that easy. My mind doesn’t work that way. I have the potential to do great things, or not so great things, but very rarely anything in the middle. I seem to be failing at acceptable.

When it comes to my two or three job opportunities that are getting closer to being real, I consider all of the elements of the role and companies. A few of you long-time readers have warned me that it would be absolutely idiotic to take on a role at a smaller company again. But – there are reasons I failed at those companies that #1, are unique to the companies (not due to their size) and #2, there are similar issues that would happen at a company of any size. If anything, I am more suited for smaller companies because I need to move fast and get things done, or else I get bored and demotivated, and that’s when I do my worst work. If I’m just a cog in a corporate machine, I might keep my job longer just due to HR policies, but I certainly won’t be helping myself or my firm.

The smaller company job is exciting to me right now because I can see many things I can do in a very short amount of time to make a huge difference. I want to compare this opportunity to my past failures at smaller firms to try to hash out the difference, and realistically explore why a smaller company is or isn’t a good idea…

My past two companies, which have ranged in size from 20 to about 100 employees, had significant challenges unique to each opportunity.

Upon leaving a smaller firm where I stayed four years without getting fired(!), I took on an opportunity I knew I wasn’t the right fit for. The head of the company was an expert in my field, and while it’s his fault for hiring me without asking some basic questions to establish if I actually knew what I was doing or what he expected me to do, I also had a boss who had a very set way of how he expected me to get my job done. I really didn’t know what I was doing and it became clear pretty quickly that I wasn’t the right fit. If I were to take on that job now I’d actually do  much better at it. I still wouldn’t be the right person for the position, but I now know enough that I could have lasted longer. I was just clueless and five months in when I was let go, it was the right decision for the business. Given the industry the company was in, I couldn’t even do the things I do best there because of the industry. It was just a very bad fit from the start.

My next job, where I stayed a year (which is respectable in startup time), I picked a company in an industry that I care about. Yet again I found a CEO who was starry eyed about me and recruited me so aggressively I had no time to discuss my strengths and weaknesses. I was thrown into the fire, but at least was given a reasonable budget to work with. But everyone at this company would agree – there are some serious management issues teetering on schizophrenic. Another trend – the head of the company had a background in something similar to my role, so he had a lot of strong opinions on how to do the job, and would basically force me to do a whole bunch of things that didn’t make sense at the expense of time to do the things that had to get done. I did fail to hire a team for a number of reasons, some of which were out of my control – the biggest problem was that the company had a lot of fundamental issues and it still does (lots of people have quit by choice over the last few months and the trend seems to be continuing.) Beyond the basic issues of the core business, the head of the company’s behavior teeters on sexual harassment (anyone working at the firm would agree) and everyone working there is so stressed and upset that they end up taking it out on each other.

Despite the challenges at the company, and it being the right time to leave by choice or by force, I learned a ton in the last year. I worked with an outside agency who taught me a lot about how to do my job. I learned how to not waste money through a bunch of trial and error and how to do things faster. I also discovered a bit about the types of people I like to manage and the types of people who I cannot manage. I learned how important recruiting is and how challenging it is at any company but – it’s actually easier at a hot young company than a big corporation or a startup that has been around for years and is on the verge of falling apart. If you can’t attract the right candidates to your firm, you’re pretty much fucked (or you’re spending a whole lot of time on recruiting that you should be spending on getting your job done.)

Ok, so why even think about going to a smaller company again? Haven’t I learned my lesson!?! Well, as you can see, a lot of the issues had at these companies were company-specific, or addressable by the fact that now I have about two more years of experience and I much better understand the bigger picture. I understand how much things should cost so I’m not freaking out every minute about budget and wasting too much money or not spending enough. I’m not saying I’ll be perfect at my next job, no matter where I go – but I do know I do my best work when I care about the product my company is making and respect the people who are making it.

The smaller company I am considering is SMALL, don’t get me wrong — there will be challenges for sure. But the founders are a bit younger – closer to my age (I think the head of the firm is maybe 2-3 years older than I am) – and this makes a huge difference in team chemistry and respect. I’ve always worked for teams where the execs are in their 40s/50s, and much older than I am. I’m fine being the only woman in a senior leadership role, but it helps with the others aren’t all dudes who are going through their personal mid-life crisis while making the younger women of the company feel uncomfortable.

What’s great about the small company is that I believe in them. I see that their product is already getting a lot of traction, and I see a lot of ways I can quickly help – and I’m super excited to jump in and do just that. I know I have some hiring to do – but I also have the momentum of the company and it’s early stage to help source the right talent. There are really two types of employees in Silicon Valley – the ones that like early stage startups and want to be part of growing something — and then the ones that want to work for a very late-stage startups or public companies that are big and somewhat stable and come with that fancy brand name and cult-like culture. It’s really hard to hire for the middle ground… the companies that are not hot, sexy startups but that haven’t made it… the ones that are dying a slow and painful death, who often have second or third CEOs who are brought in to “save” the company which had about a .00000001% chance of actually saving.

So, in short, not all small firms are created the same AND my experience today is vastly difference than my experience from a year ago. I have a fairly strong opinion on what to do and who to hire, and I won’t be floundering quite as much for the first six months on the job. I’ll certainly hire a detail-oriented person to be on my team, who balances out my big-picture strategy style. And I just think I can knock this one out of the park. If I didn’t, I’d never even consider it. But something tells me this is a really good opportunity. But I could be delusional. I could be lying to myself because it’s the most exciting opportunity, but not actually the best fit. I’m trying to sort that out.

The larger private firm is also a really good option. What I can’t figure out is how much is broken right now and how much is working. It’s not a stable public company and it’s not a small, early-stage company with the fun moments of cherishing each win and feeling part of that with the whole team (I really love that about smaller companies.) My role would be very vital to fixing some of the pieces that aren’t working right now… and I can see what those are and have some ideas how to get things in order… but once I get the basic stuff functioning, I’m not sure where I’d go from there. The role seems a bit more limiting. The company’s product, while useful and needed, is not something I can get super excited about. Maybe that’s a good thing? But I’m an INFP and I really need to feel morally connected to my work. I told myself I’d never work for a company selling to marketers again, and, quite frankly, the two larger opportunities I have are selling to marketers. I’m not sure that’s the right fit for me either. Yes, it may be more stable and it may be closer to home and the salaries may be higher (don’t know that yet) but… if I’m not feeling passionate about the product I’m just going to crash and burn pretty quickly.

There are other jobs out there — but so much of the business technology lacks the human side. I like to have that human piece to spin stories and generate buzz. The smaller firm has so much going for it around the stories I can tell, and that’s what I do best, with the right company and right stories. I think I could help all three companies but I see my value being most at the smaller firm. I think what they’re looking for and what they value is a lot more in line with what I do best — they very much appreciate that I can do all the other stuff, but I do feel like they’re hiring me for the skills I actually have, and will value my ideas and contributions in those areas vs constantly debate me and tell me I’m wrong.

So… I am most enthusiastic about the smaller opportunity, but I’m also not 100% on it. I think that the feedback from my readers warning me to not go to a small company again has merit. I hope the above explanation shows why I’m not just jumping into any smaller firm, and that this one specifically excites me for a lot of good reasons. It will be hard and a lot of work… but I want to feel inspired and work hard. I want to go to work everyday thinking that I feel good about building something great with people who deserve to be winners. Good people who aren’t sociopaths or narcissistic or delusional or suffering from borderline personality disorder. Just people who want to build something great. That’s where I want to be, and that’s why I’m excited about this opportunity, history be damned.