My last post on getting fired was the most viewed thing I’ve ever published. This one is in the spirit of “whats next?” Short answer: I don’t know. Longer answer below.

I’ve been here before. I’m approaching a dusty intersection in the middle of America. My brakes make a metal on metal dog whistle screech as I come to a stop. There’s no one around. This patch of ground is so flat you could watch your dog run away for three days. The breeze is dragging its fingers through brown and yellow waist high prairie grass. The intersection is T shaped; I could make a right, a left, or make a three point turn and head back in the direction that I came from.

Since there’s no one around, I’ll take an extra minute to consider my options. The safest one is to make a three point turn and go back the way I came. I know what to expect on that road. Every two weeks, that road will direct deposit 3500 bucks into my checking account in addition to the possibility of lumpy commission checks. I’ll be able to pay my bills without checking my balance. Most of the risk will be eliminated from my life. I’ll even enjoy the feeling of a fresh start at a new company.

Around six to nine months in, the relief will fade and I’ll start hearing the voices again. “How did we end up here again? What would have happened if we made a left or a right back at that intersection.”

As I idle at the intersection of finding another job and doing work that calls to me, I’ve got some thoughts.

Some light math. My monthly burn is around 8,000 bucks. I don’t know how that happened, but it feels like 8 million. I made a simple cash flow chart. Professor Tony Wain (accounting) would not be proud of this excel worksheet, but it gets the job done for now. If I was a business, I’d run out of money in 4 months. I’m trying to take a machete to that 8k number but unwinding lifestyle creep is hard. Life has gotten a little fancy and I like six dollar coffee.

On the positive side of the ledger, I’m working with a small severance from my last job, some savings, a wad of cash that a friend handed me last week, unemployment, and a little project that should net 1200 bucks per month. I've got a couple months to figure this out. If I need to find a job, that process can take three months (or more). I can’t start that from a dead stop in four months. But I’m not looking for a job today.

I flip to a new page in my sketchbook. At the top of the fresh page, I write “ASSETS”.

These assets are skills or circumstances that I can leverage for income. Here’s what I’ve come up with so far:

1. Leadership skills

2. Communication (writing and speaking and listening)

3. Storytelling

4. Strategy and logic 

5. My network

6. Creativity

7. Sales experience

8. Tiny but loyal group of readers

9. Fitness industry experience

10. Physical health

11. I read a truck load of books

12. Packing a cooler full of ice and beer

13. Learning new skills

14. Cooking: breakfast sandwiches. Chicken parm, garlic bread.

It’s an odd list. You can’t really plug this stuff into indeed.com and have them show you a list of jobs. But I’m not looking for a job (right?), so what could I try?

1. Offer a course on creative writing (Zoom or in person)

2. Try to sell a novel or collection of short essays to a traditional publisher

3. Help people launch and sustain podcasts

4. Get a “cottage food license” and sell breakfast sandwiches

5. Find some freelance writing work

6. Full time writing job

7. Do some content consulting for businesses

8. Write a screenplay

9. Pitch myself for a sales leadership job managing BDRs or inside salespeople

10. Offer a sales leadership course

11. Come up with a new premise for Carrot Cake and make it a paid subscription. 5 or 10 bucks per month.

12. A portfolio career (part time job paired with a couple other ways to cobble together a living)

13. Do a career restart in another field. Marketing, woodworking, landscaping

Now I can take this list and apply some filters.

I want to be able to test quickly and be nimble. I need something that shows hope of generating cash in weeks, not months. I want control of my schedule. I want to do creative work that matters to me. The only financial goal is to avoid going back to a corporate job. 

A slight sidebar for a moment.

I’ve been wrestling with the idea of having enough. I’ve always thought I needed to make 250-300k per year even though I’ve never made more than 130. As a thought exercise, what if I can only make 130k per year? Can I be happy with that? Can I feel content as all of my friends climb into higher tax brackets and join country clubs? Maybe, although I daydream about toiling away in obscurity until one day I break through and get a giant windfall.

More third grade math. 130k is 10,833.33 per month. Call it 11. That’s eleven customers paying 1000 bucks per month for a service. 110 people paying 100 bucks per month for something. 1100 people paying ten bucks per month. Or some mix of those. I don’t think it will be that clean. Maybe I’ll have 20k months and 2k months.

If you visit (this website), you’ll see that I made a little one page website offering podcast services. I’ve got it priced out at 2500-5000 bucks per month. I’ve got one customer* signed up at the low end of that range. That’s the one that should net 1200 or so bucks. Five or six more customers at that number would put me on solid footing.

I’ve started doing the work to find five more. Everyday for the past couple of weeks, I’ve sent out cold emails to marketing professionals at tech companies.

I’m targeting people by finding companies that have open recs for content jobs. I’m thinking that if a company needs a body to generate some content, maybe they’d consider paying me 3k per month to generate podcast episodes and clips for social. So far, the response has been underwhelming. I’m not sure any of these businesses give a shit about podcasts. Podcasts are hard to tie to business results. I cannot claim that you will sell more widgets because we’ve launched a really cool show. I can only tell you that you’ll have a reliable way to churn out content on a weekly basis. I tried this idea briefly at the beginning of the pandemic with similar results. I’m going to keep sending out the touches, but the lack of replies is telling. Maybe businesses don’t care about podcasts. Maybe I’m targeting the wrong audience. Maybe I have to take this idea behind the shed and put it down. Maybe it’s a fun side project and not a real business. Lot of maybes.

How did those sales leadership ideas sneak in there?

I’ve worked at a handful of companies in the sales department. From the rep perspective, quality sales leadership is rare. To be fair, most sales managers are not trained (or qualified) for the job. They are figuring it out as they go. They become a mashup of the good and bad parts of the people they’ve worked for. Of the dozens of sales leaders I’ve seen, I can think of two that I didn’t dread working for. 

Most of sales leadership is pipeline inspection and constant deal updates and check ins. There is no development, no coaching, and no inspiration. There is no listening, empathy, or humanity. The CEO doesn’t care if his VP of Sales is a quality human if she hits the number. A huge chunk of a sales job is figuring out how to tell stories internally. Stories about why a deal might not be dead. Stories about how you’re going to back door your way to your number. Everyone has a story.

 Here are some things I’ve never heard from sales leaders:

• I trust you. You make the call and I’ll back you up.

• This is really hard right now.

• How are you doing? No, Really. How are you?

• Let’s make some cold calls together.

• I know that I’m new to the team. Tell me what’s worked and what hasn’t.

• Let’s work on a sequence of three touches that will improve your response rates.

• Where do you want your career to go? You don’t have to pretend that you want my job. Maybe you want to open a bar in three years.

• What’s your life like outside of here? 

• How can we make this place more enjoyable for you?

• Let’s take three dream accounts and try to crack them together.

I don’t think I want to be in sales leadership. I don’t think I can surf or hike on a Tuesday if I’m working for a company. Maybe I could write an E-Book or release a 29 dollar course. “Human Sales Leaders who Put Up Numbers.”

So who is doing the kind of work that I want to do?

There are people who have Substack newsletters (this is a Substack Newsletter) who put up paywalls and charge 5 or 10 bucks per month. Some of these folks have thousands of subscribers (examples). What a dream. I’m not aware of anyone making 11k per month writing the kind of stories I write here. If I wanted to make this a stream of income, I’d need to get a little more serious about answering the question, “Why would someone pay 5 bucks a month to read this?”

I heard on a podcast yesterday that a woman made 260k by offering a “how to make caramel apples” course. Iphone camera footage, store bought caramel. 260k.

A glaring weakness that I have today is no real social media presence (audience). People who profit from content typically have built large followings on Twitter or Instagram or giant email lists. I struggle with this. When I spend a lot of time on Twitter and Instagram, I get angry. There are a lot of assholes with large followings. You can’t be reasonable and attract a crowd.

I snap my directional on and make a left at the intersection. It’s dark now, so I’m driving slowly with the high beams on, constantly scanning for little side roads that could hold opportunity.

Life is full of suffering, yet we soldier on.

Thanks for reading.

*Coming soon. The project I mentioned a couple times.