I have tons of debt after launching four companies. There has never been a launch that didn’t mess up my personal finances. Most entrepreneurs have no credit – I am like that as well – so I have learned to live with debt and without credit. This is what has enabled me to take risks, set lofty goals, and go after dreams that lots of people tell themselves their debt precludes.

How do I do it? It’s all mental. Here are thirteen ways to think about debt to keep it from ruining your life.

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I am in the car about forty hours a week. I hired a driver. She won’t drive all the times I have to drive. Of course she won’t. Her life would suck.

It doesn’t matter. I have to be in the car for so much anyway.

I can’t ditch my son’s therapy appointments. I need to be there to say, “Of course nose picking is like cutting.” I’m an expert on cutting. Digging out eyebrow hairs so they bleed or tearing cuticles so they hurt all day. I need to be there to translate for the therapist the world of comfort through pain. Read more

After a long break from new courses, Melissa and I did a course on how to start freelancing. This is especially timely because over the last six months while I have been rejiggering my online courses Melissa has launched a freelance business.

My first thought was: Oh. Crap. Melissa is too busy to do courses with me. But she says that will never happen.

So join me for Get the Guts to Start Freelancing: it’s a four-day online course with chat and constant chatter from me, and from Melissa who will sometimes moderate and sometimes cut me off to make her own points. You’ll learn how to make a strategy to start and create tactics for attracting more clients as you grow.

This course includes four days of of video sessions and email-based course materials.  You can purchase this webinar for anytime, on-demand access. The cost is $195.

Enroll now. Read more

One of my favorite twitter feeds is GSElevator. It’s stuff people overhear in the Goldman Sachs elevator, and most of it features bad behavior that confirms it was better for me to marry a farmer than the bankers I dated before him. But sometimes there is a gem like this one:  “The grass is always greener on the other side of the fence because it’s fertilized with bullshit.”

That is how I feel about women watching other women run their lives.

I am constantly wondering about other peoples’ lives. I’m fascinated by how we don’t tell each other what sucks about our life. We don’t tell our partners why we hate ourselves. We don’t tell our friends why our marriage or our job sucks. Read more

My personal hygiene is holding back the growth of my startup.

This month I am teaching a course: Get the Guts to Start Freelancing. If you are sick of me promoting my courses on this blog, then please note that this is not the post where I am promoting this course. That’ll be another one. In this post I am going to tell you that the course is four days and I will probably not change clothes for any of the days.

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Here’s the problem men have today: They understand how bad it feels to be raised by a dad who is never around.

There’s a generation of boys who didn’t eat dinner with their dad. Only saw their dad on the weekend. Changed schools five times so their dad could relocate to get the best job, over and over again.

Those boys are grown up now, and they are dads. And they don’t want to be like their dad. They want something different.

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This is a guest post by Cassie Boorn. She works with me at Quistic. That’s a photo of Cassie and her son. And here’s another guest post she wrote, before we started working together. 

A few years ago I targeted Penelope as someone I want to work with. Then I spent a lot of time and energy getting her to hire me. You can probably tell from reading this blog that Penelope would be a difficult boss. I work hard figuring out how to make her like working with me. This is called managing up. And these are rules for managing up that I’ve learned from working with Penelope: Read more

This year I finally admitted I’m not the climb-my-way-to-the-top type I was when I first started writing. Probably this happened a long time ago, and I was in denial. After all, so much of my identity was wrapped up in being a higher performer.

But I look at the most popular posts of the last year, and I see the change.

I remember when my agent said she could get me a $100,000 book deal to write about Generation Y. I thought, “That’s not me. I’m not even part of Generation Y.” But it was me. I just didn’t see it.

And now I see that the most popular posts are about admitting that life is not turning out how I expected. I don’t have any posts in this list about being king of the hill. But I do have a lot of posts about coping with adjusted expectations. And, based on your comments, it seems like we are adjusting together.  Thank you for doing that with me. Read more

Each of us is only as effective as the questions we ask. So understanding the process of asking good questions is essential to our success.

1. Ask questions about what you care about.
A great example of the importance of questions is the  Justice Assistance Grant which gives states $400 million to fight crime. The JAG board asks for data  on how many arrests were made and how much property was seized  – questions that inadvertently encourage states to add to unacceptable rates of incarceration in the US. Read more

You know authenticity is how you connect with people, but it’s hard to know how to gain authenticity. Just wanting it does not increase it. Also, our perception of what is authentic changes. For example, five years ago, when social media was new, authenticity was transparency. Today, with most things feeling transparent, authenticity is something more nuanced. Read more

© 2023 Penelope Trunk