Entrepreneurial sleep struggles and the sleep-whenever experiment

So we’re going to discuss sleep again. I’ll be talking quite a bit about how my life has been different with less sleep, as well as my journey back.

Before we talk about how things are going now that I’ve decided to follow my body’s rules?

Some background.

Only because I only wrote all of this down in hopes that

  1. You might recognize yourself and see that your need for more sleep is a real problem, not just in your head, and
  2. Maybe my current solution or another one I’ve tried could work for you as a fellow entrepreneur, particularly if you have a disability, apparent or not.

Things I did in the before time


Like most spoonies I’ve had a varying degree of this sleep problem for years. I’m luckier than some because I saw my spoonie issues coming and began to build an entrepreneur life for myself in 1998.

I had around a half-size business failures under my belt at that point, with each one I got closer to a viable profitable venture.

19 years later, I own a small business, and plan to re-open a second one that I had to shut down while I had cancer.

Over the course of that time, I found that a great many of the business owners I know are spoonies too, despite them not knowing what that is.

Basically if you have an invisible disability, you’re a spoonie too. It’s an important designation because it means that the normal other people expect from you is not possible to maintain AND remain in your version of a good or steady level of health.

Here’s a quick overview of my sleep issues.


Let me know in the comments if any of this is familiar.

To start with my body is still on West coast time still, 10 years after returning from Vegas to Maryland.

Before the cancer, I tended to fall asleep around 2 am. I’d get up at 9.

But with a max commute of 11 minutes to get to an occasional out of home office, as a business owner this worked for me.

With the cancer, my sleep became disrupted again.

And on top of that, the things I needed to do to make money were best promoted or marketed in the morning, live.

Some of it I could delegate or schedule. But there’s still the 30% I have to either be there for, or give up some income.

On the other hand, my most best-selling work in creating products happened at night, usually after 9 pm.

I made courses, guides and recordings faster at night. Fewer devices were on the network. The house was quiet because the kids were asleep.

What’s sleep got to do with it?


So as you can guess, this is how my sleep came to suffer, post-cancer, when I couldn’t fall asleep until 4 am.

My work meetings were during the day so I couldn’t work at night. I didn’t have the energy, and was still working a reduced work week of 15 hours.

It was enough to maintain the income I had during cancer but isn’t enough to advance it.

This was something that used to be so easy for me, to the point of taking it for granted. At least once a year, I’d make enough money from book sales to take 3 to 6 months off, if it came to that.

I’d had challenges with my health before, but had always bounced back.

After a massive sale or a small fundraiser, I’d be back on my feet. This was because I could always lean on my ability to create products for my private audience. I knew them well enough to know what to make to help them understand the latest greatest thing.

How the sleep issue snowballs


But now, I haven’t been able to create any products in over a year.

Among other things, I don’t have the stamina.

Sleep makes all of this worse.

At night on my old schedule I’d get 1-3 hours. During the day I’d be lucky to catch a nap between 4 to 6 pm.

Everything suffered. I couldn’t work more than I was now used to because I couldn’t sleep, then I became anxious about not being able to work, and slept even less.

I couldn’t not work on my main project or I wouldn’t have any money at all.

And without enough sleep, I couldn’t go without my medicine long enough to get to the level I need to reach to be able to create. And I need to be on a minimum of medication to do the things that help me think of product ideas.

It’s one thing to provide services for a couple of clients – I only need to be lucid for intellectual problem solving. The execution then gets broken down into micro-steps and tasked to several teams.

The services I’ve been providing for over a decade require thought, study and research. I go without my medications during the day to make sure I can think clearly and am at my sharpest.

It’s not so with making something from scratch.

Creative energy is different.

Having a clear thought is one matter – being able to

  • convey said complex marketing thought
  • record those thoughts intelligently in both video and written form
  • set up the sales pages and graphic art
  • plan a content path to lead people to my product

Again. It takes a different, deeper type of energy.

And with my pain spikes and the slowest cancer recovery known to man, I am making just enough to cover regular bills. While I’m not in danger of living on the street or going hungry, I have to stretch my medications, and supporting a family is harder without the extras.

I tried all kinds of things to get on a “regular” sleep schedule


In an effort to change my body’s mind, I volunteered to get up at 6:30 am to help my sister wrangle her two sets of twins for school time.

This was after I realized I don’t get up early unless I have to- that became my “have to” reason.

I figured, as in times past, my body would get used to the new routine, and my sleep would correct itself to fit into this new schedule.

The new morning duties weren’t grueling, it mostly consists of yelling “WHERE ARE YOUR GD SHOES” from my bed and monitoring the toothbrushing and clothes-wearing of the three boys.

The oldest, a girl, never has problems getting dressed on time unless she’s sick. Her issue is getting out of bed to start with.

The simple solution appears to be me playing “Juju on that beat” as my alarm.

Meanwhile, as they get dressed,  I do my first shift of work. They leave, I get brushed, washed and dressed, exercise, have a nap, do a second shift. This became my new schedule for a while.

My existing work has become more productive as a result.

But the core problem remains.

I still wasn’t sleeping. I just not-slept at more convenient times. And trapped my sleep time at a different time of day and night.

It was becoming a real issue as my still-weakened immune system now gets sick just from hearing a sneeze on TV.  As a result I am just now getting over about 6 weeks of having both a flu and a middle ear infection.

So this “get up early and tire yourself” is not only not working, it may have backfired so badly as to make me sick.

Sleep whenever: the before picture.

Before, in all the forced incarnations of trying to sleep when I thought I should, I was getting an average of about 4 and a half hours a night.

old sleep schedule
Export of my old sleep schedule from my UP3 app

The picture below is a graphic from my Jawbone UP3, which monitors my sleep, as well as my activity and resting heart rate.

I started the sleep whenever idea on the 24th. My priority became getting at least 6 hours of sleep, with the intention of moving up to 7 hours, by sleeping whenever the mood hit me.

Once I reach 7 hours, and create my next 4 products, I’ll feel like I will have the luxury of time in retraining my body to sleep in a way that’s compatible with the rest of humanity.


I’m not so sure when I look at even just the first week of results. Maybe I should just keep doing what works?

Sleeping whenever: What my sleep is like now

more recent Jawbone Up3 snapshot of my monitored sleep
Sleep looks better right?

My average sleep is now six and a half hours. Even on a stressful day, six and a half hours is a much better look than less than 5.

After about a week of sleep that makes sense, I’ve made more progress on a new product over the past four days than I have in almost two years prior.

Hopefully I’ll be able to create enough to stay ahead of the workload I’ll be creating from rebooting my product line. It’s such an important part of my business model, now neglected from years of pursuing short-term income over long term stability.

Now that I need both to live, I’ve realized that I need sleep. If you feel like you aren’t productive enough, experience has taught me that the first place to look is your sleep.

While I continue with this experiment, we can go back to the #60to15 series, and pick up where we left off in the tool reviews. In the meantime I’d love to hear about your sleep struggles and solutions.