Tag Archives: unemployment

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.



What on earth should I do?

Two companies are about 24 hours away from giving me official job offers. Meanwhile my old boss has a consulting project for me to start Monday – if I want it. I’m on unemployment now and the messed up thing about unemployment is if you take a side project that’s short-term you can end up losing your unemployment earnings (which aren’t that much at all but still) — I mean, I make about $1800 a month on unemployment so theoretically I would work one week a month and make that at my going rate… so it’s not like, the end of the world if I lose unemployment, but it would still rather suck if I can’t find consulting work and these full-time ops don’t pan out.

I’m trying to be really smart about this next job thing. And I’m really not sure what to do. I wish I was comparing apples to apples here but I’m really not. I have so many things to take into consideration. The logic side of me says to go work for the slightly larger company that is more stable and get a solid name on my resume that people will know. The passionate, excited, wants-to-do-something-i-love side of me is really interested in this opportunity to run a department at a very small company (<20 people.) One thing I would do for the second opportunity is make sure to negotiate in specific headcount before I accept the job. I’m looking to build a team, not be a one-person-machine masochist. Which is what I normally am.

I could also feasibly convince everyone to hire me as a consultant, but I’m not sure that’s an ideal route either. I mean, I’m not sure what my rate would be. My friend said I should bill $125 an hour. I think I’d try $150 and see if people would go for that. Compared to FT salary it isn’t that much w/ self-employment taxes, health insurance, buying supplies, non-covered transportation, loss of unemployment income in the future if needed, PTO & maternity leave (if provided by company), et al. Those costs add up fast. I figure if I could work 40 hours a week for $150 an hour, though, I’d be doing very well for myself. And I’m sure I’d be a whole lot happier and way more productive in those 40 hours. But I really don’t think these companies would be open to hiring me PT, or for that rate.

The problem with the small company is that it’s far away from where I live again — big red flag — but I’d also really focus on negotiating remote work before I sign on the dotted line (like 2x per week remote plus occasional longer periods to work from east coast.) If they really want to hire me, I’m going to make sure it’s on my terms. Otherwise I’ll go to the bigger company which is closer to home and that probably has better benefits since they can afford them at this point.

But — there is a part of me that’s thinking this is my last big shot to do a startup and really run with it. Yes, I’ll prob be a young mother at some point in this journey — but I can get a good year in before I have a kid right now (i mean, it takes 9 months to have the kid even if I get pregnant at some point in that year.) I can do a lot in a year with the right team. When I have a kid I’m def going to want a job closer to home and such, and there will always be those opportunities out there. But now… I just want to go somewhere where I can make some magic happen.


So many doors… but are any of them the right ones?

Amazingly enough, I have 3+ almost opportunities on the table today. Each is very different, yet they’re all generally in this field which I think I need to leave. It’s just very hard to change careers when people are practically begging you to work for them doing what you’re supposedly good at doing. Somehow I manage to interview well but it’s the day-to-day management of the details that is just not my forte. All of the opps have their pros and cons. I’m waiting on the offers to see what the packages would be, but this time around I REALLY don’t want to pick based on salary alone (yes, last time I opted for a package worth at least $40k more but look where that got me… well, $50k closer to my financial goals but otherwise back where I started!)

I hate decisions. I really would prefer to become a consultant and freelance so I could work for numerous companies and there would never be an issue with staying at a place for 3 or 6 months, as that’s part of consulting. I found it quite hilarious and at the same time disheartening when an old boss who knows me quite well, and actually likes the work I did, told me on a call the other day that managing people isn’t my forte. He also went on to tell me that it’s not good that I’ve had a series of short stints in jobs (I didn’t tell him that I was actually axed from this one, I just said it’s time to move on) and he went on and on about how bad it is to be in jobs for such short amounts of time, and proceeded immediately to ask me if I’d want to work for his company. But he does have a point – it doesn’t look the greatest to just be in jobs 6 months or even a year. In this field a year is the minimum one can do full time without seeming like a job jumper… but after a while, in more senior roles, it’s really ideal to stay longer… at least 2-3 years, if not more.

Beyond the career tenure (or lack thereof) what really struck me most was his reminder that I’m not a detail-oriented management type. The unfortunate thing is the two roles I’m very far along on are both more management positions — one is a much smaller company so there’d be more day-to-day, hands on work — whereas the larger company would probably be more strategy and then driving that to execution. And I’m still pretty certain that this whole field is just wrong for me to begin with. I just feel so stuck. I’m too scared to make any drastic changes. It seems just dumb now — even if I don’t make as much as  I was making this past year I should still be doing reasonably well. If I start over… who knows.

For being such a fuck up I’ve done ok so far but it’s time to get serious. Down to business. I can’t just keep making the same career mistakes over and over again. I’m very nervous about the upcoming negotiations with the two firms all while continuing to interview with others and to somehow ensure my old boss provides a good reference (again) even though he thinks I can’t manage a jar of fruit flies.

I try to remind myself that there is some truth to the companies I’ve worked for just being – hot messes – but it’s my fault to put myself in those situations and worse it’s my fault to not figure out how to survive them. Other people I know are just so much better at that.

The Unemployment Rollercoaster

There are so few times in life when you have your health and you’re neither in school or employed. For the lucky few who can afford a period of time out of work without a complete financial meltdown, this should be a time to stop, reflect, and even, god forbid, enjoy life for a minute or two. I really wish I could do that, but as always I’m a heaping ball of anxiety. I can’t just let go and allow life to roll me on its merry way, wherever that shall be. And all the anxiety is getting me sick, for I’m coming down with some kind of cold, because my body has finally let go and accepted its own weakness.

I don’t know how to interview right now. I have interviews — interview #5 with a larger startup and interview #2 with a smaller startup and interview #1 with a global firm. I’m a decent interviewer, but I always feel like I have to fib a bit to get the job. It’s not like huge lies — but someone may ask me if I know how to do something and I say sure and if they ask me to explain results from said thing I find some numbers that sound obtainable and throw those out there. How many leads did I generate per month? Oh, great question. What number do you want to hear that is actually something I might be able to deliver at this company, even though it’s in an entirely different market? Hmm. Even telling the truth can bite you in the ass — for at one company it might be much easier to deliver strong ROI than another. You just can’t win, but what you say at that interview, if you take the job, will haunt you forever.

And I don’t want to have to fib my way into an opportunity, or just accept the blind  delusion of some CEOs who think I’m god’s gift to this field until they’ve hired me and see my limitations. I just wonder how people who do this for a living actually get good at it. Some of the job is just mindless repetition and detail work, which I’m intuitively horrible at. But there’s a lot of strategy and execution around that strategy as well. I mean, it’s not rocket science. Why do I suck so bad at it?

For starters — the field I’m in has a zillion / infinite things you can do at any given time. This confuses the shit out of my ADHD brain. I want to do EVERYTHING! So I start a whole lot of projects with the best intention. The few that do get finished are usually pretty good. Problem is, most don’t get finished, or at least not in time. Even when I try really hard to not do this I end up in the same hole, over and over again. If I were to take a job where I was assigned tasks I’d probably be ok with that if it required some level of creativity to solve the problem at hand, but not if those tasks were detail-oriented and repetitive. I know I’ve gotten so far in my career — to a $160k salary — by just saying the right things and trying my best until the anxiety just exhausts me and I can no longer think straight and I start making one careless mistake after the next.

Some of my commenters have suggested that I move somewhere with a lower cost of living. That’s certainly an option. But I have (some) friends here. And no matter how little money I have, driving down the freeway and seeing the beautiful rolling hills at sunset with the fog rapidly dancing over them is just – worth more than anything I could pay for. There are so many reasons why I love living here. I could move, but at the least the frequent sunny days and blue skies here keeps seasonal depression largely at bay — it was just so, so bad in other places I’ve lived. My fiance hates warm weather so there aren’t many places we can go that are sunny yet not so hot. I’d like to somehow stay here. I don’t know if I can.

I guess I’ll see if I end up getting offers for any of these jobs. I’m way too over qualified for roles in other fields that I’d like to pursue, and ironically the only way to switch into a job paying less than half of what I make now is to go back to school and spend about $150k-$200k for a master’s degree. Which is also an option. Right now, I just need to relax. I’ve been getting more and more upset about this entire last year and there’s just not point to that right now. What’s done is done.  I have to just move on, and hopefully not too fast to the wrong thing, just because it’s there.



New Unemployment/Unemployed Budget

Well. Here I am. Unemployed. Since I received no severance and was not eligible for payout of any PTO (side effect of the supposed unlimited vacation perk), I’m left with my final paycheck and waiting for unemployment to (hopefully) kick in.

When you apply for unemployment they ask you a whole host of questions and I’m concerned I won’t qualify, though I should. Even if I do qualify, it’s a whopping $1800 a month (before taxes) and they make you wait a week to start claiming, so the first month is actually more like $1350 for the month. And $1350 is about how much I pay in rent. Thank goodness I’ve been somewhat smart about saving this year (I knew the job was not going to last long given how I performed with the heaping of anxiety and lack of sleep brought on by a very non-supportive work environment and a long commute I should have never signed on for in the first place.)

I thought it would be a good time to check in regarding my networth and budget. My networth goal for this year was $400k but that was a stretch to begin with (a $100k increase from 2014 including savings and interest.) Right now, counting all my assets I’m at about $350k – which isn’t bad considering the way the markets have performed this year to date. I’m sure with some better investments and less stress spending I’d be a little closer to my initial goal, but not by enough that it would really be meaningful. I have to take a moment and applaud myself for reaching $350k networth. Even though it’s not the big $500k, $350k feels sizable enough to merit a moment of self congratulations. For some reason, this amount makes me feel better about my lack of job stability due to my mental illness. While I can’t touch all that money immediately, and after taxes it would be less, if I was desperate there’s enough there to get through my own personal instances of deep depression (yeay bipolar life.) I don’t feel secure enough yet to have kids, or quite frankly, to get married (which is happening this spring anyway), but I feel like this is an accomplishment of some sort I can be secretly proud of… especially given that just 10 years ago I had about $5k to my name and was basically living paycheck to paycheck.

Here’s how the $350k breaks down:

  • $27.5k – cash
  • -$46 – credit debts
  • $153.5k – stocks (taxable)
  • $178.3k – retirement funds
  • $6.5k – 529 / grad school fund
  • $8k – approx car value

Now, my goal for the rest of the year, revised, is to end the year above $350k. This just brings me back to my older goals of saving $50k a year – which I’ve been doing for the last couple of years. I though this year given my income increase I could save a whole lot more, but you know, markets fluctuate so much, and maybe I actually bought enough stock “on sale” this year that I’ll have a really good 2016. Who knows.

The trick at this point is not significantly dipping into my cash to live between my current job and my next job… especially since I don’t know when said next job will start (or what it will be.) The $1350/$1800 a mo in unemployment is barely enough to cover standard recurring expenses, so I’ll have to dip into my savings a bit. I’m hoping that by Dec 1 I have a job so this leaves me with just 1.5 months of unemployment, which shouldn’t hurt too much. With the wedding coming up, and all the expenses for that, I really, really, really need a job – even though I admit it’s nice to have a few weeks to just stop and focus on planning this crazy event since the lack of time to do that was also stressing me out.

But I want to plan for “worst case scenerio” 3 months without a job. I’ll give myself 3 months to find something I really think I can be good at – because the last thing I want to do right now is to jump into a position where my anxiety will get to me again. I’m hoping to find something with a bit more flexible work environment – the amount of work I can get done at home in a quiet space far surpasses what I can do in some horrible open office environment filled with stress-inducing distractions. I’ve made a pact with myself that I’m not going to apply for things I know I’ll ultimately fail at given the work environment. I also am probably going to apply to grad school because I know the field I’m in now rarely meets my minimum requirements for sanity, so despite the great pay, I think I need to take a break from chasing income and now start to actually plan for sustainability. In short, I can’t be crazy mommy who gets fired from her job every year – my future kids don’t need to see that. I want them to see me in my best state – one where I actually like my job more or less. Not the me who I am now. I would never want them to see that person.

So I’m assuming I will need to spend about $2000 a month additional from my savings in order to cover everything from gas to get to job interviews to food to grad school applications to a potential trip home to the east coast to spend some quality time with family when I have the time (dad’s cancer isn’t getting better and despite that he drives me nutso whenever I see him I always think – will this be the last time?) So… say I have $5k of my savings to spend over the next 3 months… give or take. That puts me at roughly $350k at the end of the year – but I’d then be worried I couldn’t find another job. I know that I have some talent and abilities… but I just need to figure out where and how to apply them in a way where someone will pay me money to do so, and I won’t flip out after 3 months or so feeling like I’m so overwhelmed but the piles of things to do and not be able to prioritize those things or even know where to start. Yes, this is the life of a woman who has super anxiety, bipolar II and ADHD. I’m not saying those are excuses for anything – I take full responsibility for losing this job, for falling into the same pattern. But there’s a part of it that is just inherently who I am. I’m different than most people, that’s for sure. I just need to figure out where I fit.

And I’m going to be 32 in a month, which is – such an adult. My body definitely feels like I’m in my 30s — I pinched a nerve a week ago and my back and arm are still in pain. If I don’t sleep a full 8 hours a night I feel it for many days later. And don’t get me started on drinking / hangovers, oy. That’s just to say that I’m not a kid anymore. I’m a full grown adult. Looking around at my apartment I have to stop and wonder if this is what I pictured adulthood to be like. Well, I never actually envisioned myself as an adult. Maybe that’s part of the problem. But when I envisioned adulthood as a general concept, it certainly didn’t look like this — unfinished apartment, used couch that’s falling apart, bike in the corner of the living room because there’s no where else to keep it, a career that doesn’t feel right at all, getting married (ok that’s a start) to a man who also doesn’t have much of anything figured out yet either, to a long life ahead of me that I imagine will poof suddenly transform into one filled with maturity once I have my own kids (I know it doesn’t happen that way, I just like to think there’s some kind of inciting incident to finally growing up.)

Oh well. Today, I just need to focus on not dipping in too deep to my savings this year, and ultimately continuing on to my “round 1” $500k goal. That was supposed to happen next year. It won’t. But maybe I’ll get there before I’m 40.







Over and done and on to the next

While I’ll never say I was perfect at my job, my new boss REALLY didn’t like me. I believe he had it out for me from the day he joined the company less than three months ago. People respect executives that come in and make fast changes – it gives them credibility that they know what they are doing. And, looking at the scenario outside myself, AND if I was a heartless professional (i.e. the kind one has to be to survive in the corporate world, I’m not saying this is a bad thing) I’d probably make the same move. From his perspective, I was this employee who committed to a whole bunch of stuff, and then it took longer than she expected, and things were done late, and she lived so far away she came to office at 10am when the rest of the team got in at like, 8.

What sucks is that I was actually making good progress. It was way too slow as I really was learning as I went, and I made a lot of mistakes that I’d never make again. I came in and reachitected a sales database and all the corresponding marketing workflows. I focused way too much on the operations and not enough on the actual marketing. But when everything was in place and I did turn it all on, it really started to work. I could see in the system a large number of really great people who could buy our product who were engaging with our content. It was just too little, too late. And, so, off with my head.

Even though I did get a warning about 20 day ago, the actual getting fired was a bit jarring. For one, I thought I had 30 days or maybe a few more, as my boss and I discussed both 30 days AND my staying through to the beginning of November to wrap up projects. But for whatever reason he got pissed about something I did and decided that yesterday was the day. Maybe my CEO made the call – like many CEOs I’ve worked with he has a black-or-white view of the world and while he used to adore me and my work (when he hired me and shortly thereafter) I had moved over to the dark side, getting a few nasty emails from him about a press release he hated and my asking the office manager to help with some mailings, that, apparently I was supposed to do myself. I have a suspicion that they both had it out for me — they gave me a warning on Sept 23 and said I could go peacefully into the night right then and there, but I am not a quitter, so I said let me stay and prove to you I can be better. I’m so close to having things work. I’m so close to showing you I can do this.

The problem was, I didn’t really believe that. Even with the systems all set up and emails going out, I didn’t have enough content to send, or enough support to deal with the thousands of other requests pouring in — managing a series of conferences, getting PR up and running again, dealing with random asks from other teams that I didn’t plan for, et al. And, the thing is, my boss(es) really want someone who just willing to sacrifice their entire life for the job. That’s what they do, so why shouldn’t everyone else? And, in my 20s, I was all for that kind of life. I had being bored, I like feeling part of a team and helping contribute to a common goal  – so what if it’s at 11 at night and I’m half asleep and I have to wake up at 5am to get on a plane?

Now, that’s not how it would be every single day at this job, but the mentality certainly is either you’re the type to just spend every waking moment of your life working (or at least be smart enough to provide the appearance of this) or you’re out on the street.

Well, I’m out on the street. My boss set up a 3pm meeting and someone at the company actually leaked a memo that gave me a little bit of a heads up, which I am forever grateful to them for. I spent the day clearing off my computer and starting to clean out my desk. I wasn’t 100% sure it was going to happen that day — after all, there’s an event next week and I’m the only person who was going to be able to set up the booth, so I thought. I thought wrong.

He must have been really pissed at me because … he set up a 1:1 at 3pm, then at 3 he asked me if we could meet at 4:30pm and then at 4 he comes over to my desk and – out loud in front of everyone else says – “let’s just get this done with. We only need 30 minutes.” That’s when my suspicions were confirmed.

And that was it. “We’re going to let you go,” he said. I waited for more. I waited for a list of specifics which I failed to do in the last 20 days when he had told me I at least had 30. But he basically gave me the look like “you know.” Yes, I do know, I wasn’t willing or able to dedicate the entirety of my life to the job, nor was I able to successfully be about 5 other employees that I wasn’t able to hire for the team, for various reasons. Ok, this is it, I thought… what crazy paperwork do I have to sign in order to get my severance and how little is it going to be (being as I was there a year, I thought they’d at least pay me out until the end of the month.)

But there would be no severance. Clearly they don’t think I’m a lawsuit risk. They just want me out. Last paycheck, last expense check, and good day. This guy is so irrational that he told me that I should consider coming in the next day to pack up in the morning, early, so no one else would be around to see me do it – or I could pack up then. LUCKILY I had already done most of my packing earlier in the day, you know, standard fall cleaning, nothing to see here folks – what was left was just a lot of trash and work content that I didn’t want to deal with anyway. About an hour after I left I get a text message from him saying it’s a bad idea to come in tomorrow and they’ll pack up my desk and mail me things. I love how quickly he changes his mind.

The entire situation at the company was impossible. Sure, I could have done a better job, worked harder, slept less, took a 5am train and returned home after 9. I could have lasted a bit longer. But the company itself is a mess. The product has been entirely rebuilt and that isn’t going so well. Clients are unhappy. Everyone knows the CEO is crazy. I caveat that by saying all CEOs are crazy and that on its own isn’t a ding in my book. Just look at Elon Musk or Steve Jobs. The problem is that CEOs think they HAVE to be like that in order to ensure the success of their company, but not all have such inherent intuitive genius. Some are just swayed easily by whatever they hear from someone else, and suddenly the world will end if that particular issue isn’t resolved (while in reality the rest of the world is burning around them, but they have to hyper focus on this one issue to make them feel like they have control of the entire situation, which, they don’t.)

Maybe the company will get purchased by someone and there will be some kind of a successful exit, but it’s like one of those many startups out there dying a slow and painful death. I don’t envy the CEOs of these companies — they come in, usually after the founder has given up or has been pushed out by the board, and they’re handed this pile of shit to try to refurbish. These CEOs are the type that are in it primarily for the money (founding CEOs sometimes actually care about the product and maybe even changing the world.) Second and third CEOs just want to get rich, or more rich. I don’t fault them for that — trying to turn around a failing startup is not an easy task. And there are still a number of people employed by the company, so this CEO is day in and day out fighting for not only his shot at wealth, but also their livelihood. It can be an admirable position.

The problem is more often then not, the new CEO isn’t able to recover. It’s kind of like handing a kid a broken toy and seeing if they can fix it or have fun with it. Maybe they’ll turn this broken toy into something amazing (maybe even something better than it was meant to be) – but – really, you’re probably going to end up with a very frustrated kid having a temper tantrum and throwing the broken toy across the room once he realizes it’s not at all salvageable.

That said, I did respect the CEO of this company because he was handed a broken toy and sold said toy to some pretty big, well-repected toy buyers, so to speak. He works his ass off and for that I can’t not respect him. And, despite his having some pretty unrealistic expectations when it comes to the performance of the team, I can’t fault him for pushing everyone really hard. His management strategy is push people as hard as he can until they break. Make the ones who are working hard feel really special (i.e. CEO is paying attention to you and “invested” in your success!) Then people get super burnt out and either they leave on their own accord or, in the rare case that someone stays because they refuse to quit or move on, he gets someone else to fire them (i.e. new boss, three months later, hands me the ax.)

Well, here I am, unemployed – yet again – but I feel ok this time around. I’m actually in a much better place now than I was a year ago because I learned A LOT over the last year. I have been talking to a few companies while I was still employed so I want to move quickly on those opportunities. I also feel like I need a break. I know it has been just a year since I was last unemployed and it’s embarrassing that I’m this tired and burnt out right now,  but I’m this tired and burnt out right now. I threw out my back/neck/shoulder/something last week and even though I sleep at least 7 hours a night I’m always about ready to fall asleep. I can use a week or two to recharge and hopefully will be ready to head into the next thing.

What I don’t know is what that next thing should be. It’s one thing to be recruited for how great I look on paper, it’s another to be able to actually execute and be successful. I don’t want to jump into yet another situation where someone has convinced themselves I’m so great when in reality I’m, well, not quite all that and a bag of chips. Or maybe now that I’ve had some more experience I can be better. I did learn a lot. I see the bigger picture more clearly. I understand the framework of what needs to get done to be successful. But if, at the end of the day, this entire field isn’t right for me, and I’m not right for it, then should I really try to stay in it just because it’s the only place I can get hired? I can take some time off… take classes… figure out who I am and what I’m good at…

I’m still planning to take the GRE soon and I still have my grad school applications in process. Maybe that’s the right way to go. I feel like I need a change. Maybe it’s just a change of company. Maybe it’s a complete 180. In any case, I guess I am relieved right now that I am no longer struggling to promote the wonders of a broken toy that may not be at all fixable.




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.

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.

Unemployment: Month Two Begins

Where did August go? This is a question I ask EVERY August, but this August the disappearance of the month had more significance than the typical summer conclusion. As you know if you’re a returning reader, I lost my job the first week of August this year. I showed up at work one day and was told it just isn’t working out, was given a month’s severance, an amicable parting, and I was one of the 6.2% of Americans out of a job. Going through the five phases of unemployment has been challenging for me as I sit and apply to job after job with nothing panning out yet.

I’m still keeping my chin up… after all, it has only been a month… but looking at my bills piling up and my measly unemployment check I know I have to find work stat. The way unemployment works where it penalizes you if you get a temp job that pays less than your previous job is really unfortunate. In fact, instead of encouraging unemployed individuals to work part time while seeking full time work, it effectively says that you will lose your benefits if you take on any work that isn’t equal to what you were doing before, at least in terms of pay.

That said, $1800 a month, pre-tax, is not going to cover my fancy lifestyle… you know, the one where I pay 1/2 of a $2350 one bedroom, 850 square foot apartment in the Silicon Valley suburbs… and $400 for COBRA… and $100 for car insurance… well, there goes all of the unemployment money and then some. In many regions unemployment income at least covers all the basics, but here it barely covers my rent. I really need work, stat.

Unlike last time I was unemployed many years ago, just a few years out of college, this time around at least I’m landing interviews. But they aren’t going anywhere. I am struggling to get past that interview stage, mostly because my experience isn’t focused enough. I’m really not sure what to do – other than keep applying. I’d like to freelance and build a consulting career – but to do this I will basically have to give up my unemployment income and likely earn less w/ self-employment tax and such on a few small gigs until I can get enough work to support myself.

In order to freelance successfully I’d need to bill $150 per hour and work 40 hours per week, with a little wiggle room for weeks without 40 hours of work. That actually is somewhat doable – I can bill $100 per hour to start and raise it as I build my portfolio of happy clients. I’m currently designing two friend’s small business websites (for free) to get some samples for a portfolio to show both my copywriting and design chops. But basically I’d want to get to the point where I was making $100 – $150/hr and working 40+ hours per week. If I could do that life would be perfect.

However, right now I’m focused on applying to FT jobs and seeing if I can land any that I’d want to do… all while building up a portfolio of design and copy work so perhaps I can get some actual paid clients when my unemployment runs out, if I don’t have a real office job by then.

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.