I’m trying to gather up to have the courage to write an honest blog. I started it to help others get through some of the “tough stuff” I went through. I keep wrestling with should I? Why would I want to tell everyone about my challenges? How do I make the leap?

I can’t stop thinking about a potential investor who is trying to get me to sleep with him. I live in Silicon Valley and he’s an active angel investor with a great reputation. So, to say I was excited when I got my first meeting with him would be an understatement. He’s personable and immediately seemed interested in my company’s vision.

Our first couple of meetings were all business. Then he started sending me flirty texts. Then he tried to kiss me.

The truth is I want to work with him but I have no interest in sleeping with him. I’m now worried that we’ll never be able to have an exclusively platonic business arrangement because he’s crossed the line with me. I’m also worried that he’ll back out of funding my company or worse yet, potentially poison the well with other investors by saying negative things about me if I don’t go along with it. People around here are so fickle that all it takes is for one “popular” investor to say an entrepreneur is incompetent for that to become accepted in the echo chamber.

So, I feel torn. I either shut him down completely and risk his wrath, or literally “take one for the team” and start sleeping with him in order to get continued access to his contacts and money.

I am an avid follower of your blog and your very pragmatic approach to life and work. I wondered whether you had any thoughts or advice on how to strike the appropriate tone when inviting someone for a networking lunch.

I am a junior/mid-level (female) associate working for a law firm and have been told that it would be good to reach out to some of our client contacts and to develop a more personal relationship with them. In attempting to draft the email invite, it struck me that it would be very easy to use an inappropriate tone, especially in light of the fact that the intention isn’t to discuss business, per se. Given that I am a woman and the contacts are predominantly men, I would also want to guard against coming across that the invitation has a romantic element to it. Or do you think I am overthinking the issue?

I’m a medical student in Ohio, and I have a question for you about networking. As a graduate student, I have had a hard time meeting people outside the medical profession who are doing unique and interesting things in their careers/life. I want to know more people who have a different perspective on life than I do and who push me to have experiences I wouldn’t have otherwise had. If I am networking for that purpose, what kinds of events can I attend or organizations should I join to facilitate that process?

I live in Nashville but want to move to New Hampshire to be close to family. On my resume, should I use a family member’s address (near the job) instead of my own? If so, how do I talk about it in an interview?

I’m in the process of revising my resume and your advice is blowing my mind because it makes so much sense. Thank you for pointing things out and being funny about it.

Here’s my question: Your advice seems focused on the business world and I work in the nonprofit sector. How different are these worlds, really? Are the same recommendations transferable to those of us working at relatively small nonprofits? There is so little room for growth in most of the positions I come across, but the only other option I can discern is to job hop. How would you advise young twentysomethings to advance their (my) nonprofit career?

During our coaching session, you said I should be working at a startup. But I don’t know what sort of position I should be looking to apply for. So the question is: What sort of position should I be looking for in a startup? What sort of position is ideal for me? Will just any position do?

I’m 29. I’m pretty sure I have Aspergers and I’m pretty sure my mom does too… I was doing research because of the latter (my mom having it) before the first (me having it) slapped me hard across the face. Not that I’m upset by it. God no. In a way I’m thrilled to finally read about others with VERY similar quirks. I find myself suddenly obsessed with this aspect of my life.

My husband thinks there is no reason for me to get a confirmed diagnosis. He doesn’t mind my antics and what will it really “do” other than jack up our insurance premiums. I did take the Aspie Quiz and a few spectrum quizzes online and I had borderline scores. Should I just go to the doctor?

Something that’s been nagging at me recently is how much younger I feel than my professional counterparts. I’m new on the job at full-service agency – I’ve previously only been in the digital space. I think most ad agencies skew young, but mine has been in traditional media for over 30 years and has a LOT of industry veterans.

I’m younger than virtually everyone I’ve interacted with so far, by quite a wide margin. I feel very self conscious of that fact when I’m in client meetings, speaking with vendors, and brainstorming with my creative team

Do you have any advice on how to feel confident in these situations? I’m terrified of somehow losing the respect of my cohorts by doing something inadvertently offensive or immature, as viewed by an older demographic.

I wish I’d seen your blog and had a wider, less fearful view of the world in my 20s. I was just trying to get out of poverty and then get out of my head, so I followed my scholastic abilities right into nowhere with an M.A. in English and lots (lots) of debt.

I’m a really good poster child for your warnings.

What if you’re in your mid-30s, and you made the wrong mistakes (or took no risks other than borrowing on the future) and you find yourself entrenched? I (and probably lots of others) could use your no-holds-barred take on it. Planning any Make the Most of Your 30s When You Didn’t Make Your 20s Count seminars?

©2023 Penelope Trunk