Here are three ideas:

1. Find the person who is in charge of the area of the company where you want to work. You can use LinkedIn for that. And contact the person. Let them know you want to work with them and ask them to keep you in mind. Then email periodically to check in so you stay on their radar. You can also email them with an updated resume if your resume changes while you’re waiting. It’s good to say, “I just want you to know about this recent accomplishment… and I’m still looking forward to interviewing with you when the time is right for the company.” Something like that.

2. Send an email that is essentially a pitch to do consulting. Show them that they need you to solve a problem they didn’t know they had, or they didn’t realize would be easy to solve – by hiring you. You can start as a consultant and get them to hire you full-time later, or you can convince them in the interview that it’s a full-time position.

3. Work for free at the beginning. At a very small company there is often a need to hire someone before there is money to hire them. If you get a foot in the door before there is money, and you do a good job, then when there’s money the job will already be yours. And bonus: you’ll get extra stock options for working for free.

I have bipolar disorder. If my meds are working and the stress level is reasonable (I can accept a tight solid well defined deadline) I deliver superior work. I am a systems engineer and damn good at what I do. I have received national recognition for a system i built. I developed a software architecture that goes to sea with every Navy aircraft carrier.

But when the meds are wavering, and somebody proposes something bat shit stupid, I lose it. The manic part of bipolar kicks in and I am furious, angry, rude, throwing things, and generally being a 100% walking tantrum time bomb.

I have never held a job longer than 3 years before completely alienating everyone in the company or having a meltdown severe enough to either get fired or decide to move myself along.

I have not only burned bridges, I have nuked them. I can’t go into consulting. No people skills for politics and networking. There are pretty much only three major corporations in my area of expertise that I haven’t worked at and they do a lot of defense work. I do not want to design something that kills people and I don’t want the hassle of a security clearance.

And I have just been laid off.

I need some advice.

I am in a serious dilemma in a crossroads in my life. My dad is an old school, wealthy conservative who wants me to join the workforce like he did and slave away my life to something I don’t necessarily feel good about. I can’t spend my life in a office, I simply can’t and I know this deep inside me.

My true passion lies in one thing- Poker. I have studied and played the game since I was 13 (I’m 22 now) and I have no doubt in my mind that it is what I want to do with my life. Don’t misjudge my passion though, it is not solely in pursuit of money. I have fallen in love with the game and the people. When I sit at a table and watch and study the people across from me I feel at home. I am competitive and intelligent, and I always have had a fascination with observing people and what drives them. I also love to meet people and be social. There is no better place to see every kind of person than at a poker table.

I want to watch people and guess what they are thinking every single day of my life. I want to die on the felt.

Here is the problem: I have one semester left in college and I had to pay for it on my credit card because my dad was not happy that I failed a class. I have always done well in school, but I find undergraduate school very pointless. I have learned nothing in college and I struggled to put any focus into it- I have always spent my time reading books about succeeding at poker. I am in debt and have no money to pursue what I want to and my dad won’t help me at it because he is severely against it.

Gambling has always been an iffy career choice, but the game, Texas Hold em, has stood the test of time and feeds many, many people as a career. My dad doesn’t believe me and won’t help me.

How do I get away from my debt and embark on my true passion?

– Anonymous Poker Player

Your post titled How to Pick a Husband if You Want to Have Kids really reasonated with me.  Well, half of it did.  I already have a husband, and I’m 31 years old.  I’m an ENFJ, so a lot of my self-worth comes from my career achievements (I’m a lawyer), but relationships are very important to me too.  Not just my relationship with my husband.  This is going to sound borderline sociopathic, but I get excited when I’m able to make a connection with an interesting person who is really introverted.

Anyway, right now I am trying to assess whether I should have children at all.  My husband definitely wants them. I think I want them too, but in reality, I know I would really struggle, especially the first few years because I would have to compromise at work.  And he makes about twice as much money as me, so I would have to be the one to take the longer maternity leave and work around the nanny/daycare/whatever schedule much more than him, at least for now.But if I decide no kids ever (leaving aside the damage to my marriage that would ensure), how do I know I won’t wake up when I’m 45 and really regret it?  My personality makes me think that would probably happen.  Then again, if I don’t have that strong urge to be a mother now, will I ever have it?

People constantly say I’m really nurturing, and I’d be a great mom.  My own mother died when I was 22, so I don’t have a great sounding board for this stuff.  Part of this may be coming from me seeing friends have babies and struggle with it.  Three of my best friends from law school had kids within the past year, and all three tried to go back but quit working entirely within the first year.

What is your advice for women like me who are already pretty far into their careers and did not take your advice to have kids early?

I feel stuck.  I have been doing consulting in the Big 4 for around 10  years now and it’s just getting old.  I took the test and I am burnt out.  I took the other test and it appears that I may not have a good job and then I took another test and it shows me that I am an ISTJ. After you get the  result from that personality test it provides links to jobs that may be good for that type and I am already in those jobs and have been most of my 13 year career.

I feel like I have been trying to get out of consulting for years now, but now that I look at the openings that exist in my market that are outside of consulting, it appears that I don’t have the skills to do those and it feels  like consulting is the only thing I can do (which is not the case….I’ll admit to having a broader skill set than just being a consultant).  I don’t know where to start to get unstuck.  I need to reinvigorate my career and find interest in what I do or I need to find something else.

I am risk averse though.  My wife quit work 3 years ago to stay at home with our four kids.  We live comfortably on my salary, but I can’t take a massive pay cut to get into something that would potentially make me happier.  That will just lead to more stress.  Also, I am rooted firmly in Columbus.  All of my family is here and it’s a good place to raise a family.

I need to find something where I get some kind of fulfillment.  Telling  people all of the things they do wrong and how they could be better isn’t doing it for me lately.  I’m 36 and I feel like I hit a wall.  I am  unmotivated and constantly thinking about how can I get a new job that will provide something closer to an 8-5, will keep me off the road and will let me be more present in my kids lives.

My hope is that someone else has emailed you about this before and you can just copy and paste that answer here, but I know one size does not fit in with career advice.  I ordered a couple of the books you referenced on your site as well, so I am hoping that they provide some guidance or perspective.

Any insight you could provide would be much appreciated.

I am a mother of three children under four years old and I am currently searching for a job. I just got home from an interview for a corporate job with a company I’d love to work for, and the woman screening me asked me several times about how many kids I have, how old they are, what my feelings are about leaving them with a caregiver all day, and so on.

I did not volunteer this information, it came up because she asked why I left my old job (my last company folded just as I was leaving for maternity leave). I found it hard to tell whether she was asking this information because she was unsure about my ability to do the job, or whether she just wanted to talk about her own maternity leave and desire for more kids.

If I pass the personality screening test I wrote today, I will have an interview with the chairman. My question is, how do I address questions about my family size/future reproductive plans without saying, “That question is illegal” or “That’s none of your business”? Please advise!

 

I was in a gender harassment situation that I left about two years ago, and did not really think about my future as I was exiting the situation. I have had a lot of personal trauma around the experience, and realize that I can’t use my last job for reference even though I was there for five years. What should I do? I still need to be able to work.

I’m in my mid-twenties and I’ve found that whenever I start a job, after a few days or so, I start feeling trapped and stuck.

I fear the regular routine of the job, being stuck in the 9-5 (or whatever my hours are) and being forced to work for the money versus doing something I love with a mission I care about. I’ve tried working for things that I believe are doing great things for the world (kid-focused startup and working with kids, which I’ve learned I’m not good at) and I still feel like that. Any kind of job with routine (even varying retail jobs and the like) scare me and thinking about applying to a job with more challenge in it (not getting that out of my current job) but that same routine worries me that I’ll be stuck there for a year or two working on building my skills for the better but still trapped inside a prison even if it is at a well-funded startup.

I’m an INFP programmer who loves logic and hopes to start my own startup someday as I get frustrated with not being able to make my own decisions. I’m not sure if I should go forward with my plan to find a job with that routine while I get great to build my skills for my own startup someday or if I should try to find something without that routine and if so, what? It doesn’t feel like most people have that same reaction to the stability of doing the same thing every day. About the only thing I know is I’m sick of not having money and I need to find something that allows me to have that. What should I do?

I was wondering if you had any advice at all about how you overcame eating disorder/ other problems when younger? 

Because I’m 21 and bulimic and kind of like a failed university student, as in I’m meant to be in my fourth year now of Arts/Law in Sydney, but I haven’t completed a single subject this year and have a history of withdrawing from subjects/ only doing part-time loads because I essentially feel afraid that I’m not going to do well enough so I don’t even try.

And I’m kind of at a point now where it feels like my life is over, and I have no future in anything, and I’m fat, and can’t seem to do anything and that I’m completely alone (even though I somehow have a really lovely boyfriend, but we are currently fighting because I keep feeling like he doesn’t want/ like me because I don’t feel worthy and he feels really upset that I don’t believe his words/ actions that are apparently evidence that he does like/ want me.)

I am on the 6-8 week waiting list to go to a residential/ inpatient psychiatric hospital to try and deal with the Depression/ Bulimia. But still, until then, and even after then, I just don’t understand how/ what I’m meant to do?

I am a 41-year-old single mom who needs to change the direction of her working life as a matter of mental survival. I’m a classic ENFJ kind of person and have been working behind a desk in isolation (I work in a suite of offices but the nature of our work is to remain quiet and alone) and it’s been wearing down my sanity.

I am absolutely in love with advertising and have always been but when I was young I didn’t choose to study it; it was too intimidating for me then. I’d love to be an ad account executive someday but getting started seems impossible from where I’m sitting. I’m reading everything I can get my hands on (marketing, too – it’s much drier but important to understand the basics) and bothering ad people for advice on how to get my foot in the door.

I have about two years to update my skills (before my daughter graduates from high school and I can focus on a career and/or live wherever I need) but very little money in which to make that happen. I can’t be a full-time unpaid intern; I have to pay bills and feed two people. I can be an evening and weekend person who is poorly paid, but with the abundance of free labor out there it’s tough.

I have a BS in Psychology, an MSW in Social Work and a strong background in writing and research. By nature I’m a collaborator, diplomat, convincer and intuitive, but those qualities can’t be put on a resume. I am not stubbornly stuck on working in advertising; something that is stimulating in a similar way would be wonderful, as long as it’s focused on people and ideas.

If you have any thoughts or advice for me I would very much appreciate either.

©2023 Penelope Trunk