What makes a question a terrible question?

Yesterday I needed a few brilliant ideas so I turned to my chat box and saw who among my tech connections are online and it happens that a social media “big shot” was online so I wrote:

“Hi [name]
I was wondering if you could share some crazy ideas. Like what’s the craziest thing you’d do for something you’d really want?”

I fired up the question hoping it was interesting and thought-provoking. I was totally taken aback by her answer:

“What made you think I would share ideas with you?”

I told her I’m sorry if she doesn’t want to answer.

Now I get it, maybe she felt insulted and violated that she’s someone that has mastered her skill. And maybe I have been stupid to ask for her ideas when she’s actually paid to give people ideas. But I must tell you that her response hurts because I really look up to her.

Penelope, I wonder if is that how most “big shots” really respond? Like when a blog reader asks you a question, would you feel insulted that I solicit your opinion or idea for free?

I would really appreciate your comment on this. Perhaps you could shed me and your other blog readers some light as to when is it good to ask questions, or is it even okay to ask professionals like her when she does consulting for a living. I thought it was an innocent question, but what do you think?

Boring job in Ohio vs Dream job in San Francisco?

I have been reading your blog for a while and have found your advice to be incredibly useful.  I recently found one of your posts from 2011 where you talk about relocating to Hermosa Beach.  That post hit very close to home for me because I’m currently going through a similar situation (although I don’t have kids).  I was hoping you might be able to offer a little quick advice.  No one else seems to understand my situation.

I’m a 35 yr old engineer and moved to the San Francisco area in May of this year.  I was laid off from my old job and luckily had an offer from a couple of guys that asked me to help them build a small search startup company.  I make about 150k per year along with equity in the company that would be worth quite a bit in several years.

I don’t mind SF, but I’m from Ohio and have Midwestern values – so San Francisco is a little different than what I’m used to – but it’s tolerable.  My original plan was to move there for 4 years, collect my equity and then leave.  However, recently my old company offered me my old position back at a salary of $108k in Ohio.  That’s a reasonable salary in Ohio, but the job in California is more enjoyable.  It feels good and exciting to help build a company from scratch.

I am very close with my mom and sister  (who both live in Ohio).  My dad passed away 2 years ago from years of medical problems, so we have a close bond due to the trauma we went through.  Needless to say it’s difficult moving away from people I love, especially my mom since she’s getting older and starting to show signs of medical problems.

I don’t want to regret using 4 years for a great career at the expense of any memories I could be making with my family.  Although, it’s difficult to pass up a career opportunity that could be worth several million dollars in a few years time.

This decision has generated a lot of anxiety.  I’ve talked to my therapist as well as others who don’t seem to have a good perspective on the situation.  I feel like you certainly understand the difficulty of this scenario.

If you have any advice or comments, this Midwestern guy in San Francisco would forever be in your debt.  Any help at all would really help me.

Thanks again for all the writing you do, as it’s really helped me in the past.

Which business idea is best for me?

I always thought I’d have my own business by now, but life hasn’t worked that way. Specifically my wife and I had a baby and I wanted a proper job.

Now my wife wants me to start a business that will let me leave my job. She has a point, because I’m not one for sitting at a desk from  9-5. Yes, I hate it. But I would need to get a good deal of cash into that business at the beginning, and we don’t have much savings.  I have a few friends who said they could help me get investors, but I’ve seen all the trouble my friends had getting investors and I don’t know if I could do that.

 So I think I should go with a business idea that my wife and I could do together, for fun. I wouldn’t need to put money into the business. Well, we would have to have a little money, but we could use some savings. It’s just that I don’t know if I like that because the business would not let me quit my job. And my wife is pretty busy, but she likes projects.

You’ve had a lot of businesses yourself, Penelope. Do you know which business would be best for me?

Answer from Penelope:

Your goal for starting a business is to enable you to get out of going to an office from 9-5. That’s a good goal. And the smaller business idea will not meet that goal.

It seems that the only benefits to the smaller business is that you and your wife have fun. But you don’t need to invest your savings in order to have fun. And I’m sure your wife can find a project for herself without you starting a business for her.

So I think your real question is how can you gather enough funds to get the bigger business off the ground.

You are right to think that doing that is difficult, but starting a business that needs funding is often the most low-risk option on the table, and I think that may be true for you.

You have friends who understand the investment community, so it’s not outrageous to think they could guide you. And don’t underestimate the need for a guide – the startup funding community is relatively conservative with stringent rules

The game of launching a business is doing as much as you can to mitigate risk. So, for example, its risky to start a business to get out of your office job, but it’s riskier to plan to spend your life in a job you hate. Here’s a blog post about mitigating risk as you start a business

You’ll have an easier time beating out the competition if you stick to something you have expertise in. So your business should be at the intersection of the idea you like and the expertise you have. You can find practical examples of leveraging your expertise in the book The Business of Expertise, by David Baker. 

Don’t shy away from borrowing money. There’s a reason that most entrepreneurs have bad credit— you have to use anything you can get to keep your business from going under during those early, fragile months. That said,  business owners who have a plan to be profitable often qualify for fast business loans.

If this is all making you sick with stress, try a career change. Just because you hate one job doesn’t mean you’ll hate them all. I would not recommend going back to school for a graduate degree — way too large an investment for something you’re not sure of. But going to a career development site that provides you with a mentor in your field is a good way to make the career change less difficult by helping you to create a network to pave the way.  NYICD does a good job of providing that service. 

And remember that there is no way to live a life without taking some risk. When you ask people at the end of their life what they would have done differently, they almost always say they would have taken more risks. So instead of avoiding the risks of doing the business that meets your goals, try thinking in terms of intelligent risk-taking and then you’re not likely to regret the outcome, no matter what it is. 

Do I have a good plan for an online business?

I launched a website very recently for women starting over in mid-life. My tagline is, “Be Your Own Rescuer”. I want to create a community of support and information for women starting over at a point in their lives when they thought they would be settled. I will offer entrepreneurial opportunities, feature other women who’ve been through it, a blog, private Facebook community, etc..

When I was in that situation, I was in despair. After my divorce I thought all the good in life was behind me. But I started cleaning houses and then I realized I could grow the business by hiring people. So I quadrupled my sales and I have ten employees. Now I want to do more. I want to show women to know they don’t have to settle for the crumbs of the life they lost.

A few things I’m working on:

I am creating a course on how to start a cleaning business, with support from me through the process.

I am also creating an 8 week group coaching course for these same women. At the end of the 8 weeks, I want them to have a plan and know what next steps they will take toward creating the life they want….

My first step is putting a bunch of irons in the fire to build a mailing list, direct them to my site, by offering freebies online through Facebook ads and instagram. Possible example: Offer the overview module to the courses for free, save the meat for the paying. Create freebies my target would be interested in: controlling negative thoughts, overcoming fear and worry, 7 days of radical self-care, the number one thing I did that changed everything, how I went from homeless single mom to successful business owner with healthy, happy, grown sons, “Be Your Own Rescuer” – how I rebuilt my life in midlife, etc….

I could also join online groups catering to my target market, get face-to-face with divorce recovery groups, addiction recovery (addiction and single mom can go hand in hand at times…), single moms groups. Write blog posts relevant to my target, share them online..

My question for you is: Do you sense that I am on track with all of this? Is there anything that jumps out at you that I’m veering off-track with?

I have a job in sales and I’m going to fail

I have been trying to get involved in my school newspaper, at a university. I made a point of saying I want to be a writer but they put me in sales. Should I tell them I’m not good at sales? I’m an INFJ and I know I won’t be good at selling newspaper ads.

Is it time for me to take a break?

I really enjoyed your recent blog post about taking a break, but I was wondering what a break that is not constructive looks like? I’ve been thinking about taking a year off of work to go to grad school, or to travel, or to do both, but, as a longtime reader of your blog, I know that you aren’t a fan of either. Do you have any advice for a way to structure the break so that you end up in a better place on the other side of it?

I know that I’m approaching a point in my life that I need a break and to change, but I’m not quite sure that grad school/travel would be a way of avoiding problems instead of changing in order to be better able to face future problems. If it helps, I’m an INFP.

What’s the best job for a perfectionist?

I’m an ISTJ. My company told me I need to increase my social IQ in order to advance. I am not sure how to do that. And I’m not sure if I want to. What jobs do people like me usually do?


It’s hard to be a perfectionist at work because most peoples’ jobs do not require perfection, so you are not evaluated by how perfectly you do something and you are not rewarded for the extra time you take. 

Especially in management, perfectionism is looked down on. So people tend to not value perfectionism. Making big decisions with very little information is what people get paid the highest salaries to do. And that’s the opposite of perfectionism. Even in accounting, the people who get paid the most are valued for their understanding of the gray areas of accounting which have no clear answer. 

So, keeping that in mind, it’s important to find a job where the management team cares about being perfect. Because then the culture of the company will include respect for people like you.

An example of a place where management cares the most about the product being perfect is online gambling. Because if there’s an error in the code, the company loses a lot of money. I coach a lot of ISTJs who write code for gambling sites. That personality type has a strong bent toward honesty and justice, so you’d need to be careful what sites you work at. Here are the best online casino reviews.

It’s true that a lot of perfectionists work in science. But remember being a scientist in academia is mostly writing grants and not perfectionism at all. However doing the actual lab work is about perfectionism. Here’s are the best places to get lab jobs.

Sometimes perfectionism is a sign autistic spectrum disorders like OCD. In that case, the best sort of job is one that is repetitive and very clear cut. While some people would get bored at that sort of job, people who  have an obsessive need for perfection find these jobs calming. Here are the best jobs for people with OCD.

Finally, perfectionism is not something that is good for anyone. Being perfect sometimes is admirable, but perfection can also be crippling. Needing to do everything perfectly is often rooted in insecurity and anxiety  and you probably need to address it. Here’s a post about when perfectionism is a disease.

Whats a good career for an idealist?

Hi. I just graduated high school, and I’m undecided and that’s why I decided to go to community college. I’ve always thought about becoming a teacher but I’m unsure if that would be right for me or if I should pursue a career in the health field like a physician assistant. I’m a romantic at heart and I just really wish I could just be pragmatic. It’s a blessing and a curse I’m too idealistic and that’s why I think I have such a hard time finding a career.

How do I apologize for being a jerk? (I have Aspergers)

I am a female with Aspergers. I think my mom and my sister have Aspergers, too. And we all have the same problem: we can greatly offend people by the things we say and how we say them. In talking with each of them, they have no idea that they are doing it and they say they don’t mean to offend. I physically cringe when I hear how they talk to people – even though I know I accidentally do it, too.

I don’t tell colleagues and friend groups that I have Aspergers. I know to look people in the eye when in conversations. I am pretty decent in one-on-one conversations when I pay close attention to personality type and what the other person needs from me and the relationship. I am very bad at reading people’s intentions.

In my adult life, I have jumped from friend group to friend group. My mom used to tell me that I wore people out. I’ve gotten fired from every job – which I think is a combo of me being an ENTP and having Aspergers. I feel like I leave a wake of destruction in my path from saying exactly what I am thinking. I’m generally a friendly and enthusiastic person, so my harsh comments tend to really catch people off guard. So, people who liked me at first will distance themselves in a hurry. Or, I’ll be so embarrassed that I hurt someone’s feelings, that I’ll distance myself.

I’m getting better at keeping my mouth shut by understanding personality type and group dynamics, but I know I will always make this type of mistake. Sometimes I will know immediately that I was a jerk by the look on someone’s face or shift in body language. Other times, I think I was just stating the obvious and everyone sees the same thing I do, but later it will become clear that I’m out of step with the rest of the group. So, I need to learn how to mea culpa gracefully to someone in the moment or later when I’ve realized I’ve deeply offended someone.

Do you have suggestions?

I’m sick of dealing with incompetence

I’m an INTJ, and I have a quick question.

I’m a Ph.D. student of theoretical physics and as usual, I discuss my research with my supervisor. Because she doesn’t bother to get into the detail of calculations, or maybe because she doesn’t care enough, sometimes she makes obviously stupid comments, and such things make me angry a little. So I feel she thinks I’m arrogant, even if I don’t get angry and try to explain (explaining stuff is a little hard for me…). But I’m not. I do appreciate when she has some good comments (which she does sometimes…).

So can you help me to avoid such misunderstandings?