Working too much

Listening to the recent podcast episode got me thinking about this. Ian and Butov were both talking about how they basically worked too much and couldn’t comfortably not work even when they don’t have to.

I’ve been beginning to see a similar pattern in my own life as well.

I feel like lifestyle and freedom of schedule are kind of a core focus for bootstrappers like us. So I’d expect that for most of us, our goal is to be free’d up to work less.

But at the same time it seems like it’s actually hard to focus on things other than work.

Do you think that you work more than you need to?

Yes, is the simple answer.

For me, I still have a day job as a cubicle monkey, so evenings and weekends are the only times I get to work on my own stuff. Which means I’m working all the time, 7 days a week.

My planned plan is to slow down once my own gig generates enough to support the family, but that’s taking longer than I thought (surprise :smile: )

I haven’t listened to the podcast yet, but I’d guess once you get used to working long, it becomes a habit that’s hard to break.

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I think that’s basically what happens.

I mean in your case you have a reason why you’re working nights and weekends so I wouldn’t necessarily say you’re working more than you should.

That’s what I’ve been doing for the last 2 years. And now that I am making enough with the business, there are atill a lot of reasons why I feel like I need to keep working a lot.

And it’s hard to distinguish sometimes between which of those things are legitimate reasons.

But then there are guys who definitely don’t need to work that much any more but still do and admit that they just don’t feel right if they’re not working. I guess I’m hoping that I won’t ultimately get all aught up in that.

Rob Walling seems to do a good job of balancing things out. I think he takes a 3 day weekend every week and goes out to the coast with his family which is pretty cool.

Then again he also dives into new projects like drip which I’m sure he doesn’t need to but does because it’s fun and challenging.

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Overworking yourself is the first step to failure in business. You can’t do your best if you’re permanently stressed out. Don’t check email in the evenings. If you’re only 1 or 2 people, don’t provide 24/7 support. It’s ok. Customers understand. It helps to not have a mission-critical product (if Time Tracking goes down it’s annoying but people can take a note on paper).

You didn’t start a company to die of exhaustion. Your health, family and social life is more important than 5 minute support response times and a 100% uptime guarantee.

Quoted from Mr Fuchs from one of his posts-to-keep. Also WiseCash (by @thibaut_barrere ) or any other tool that can help you to forecast your revenue or ‘how much have you accomplished of your yearly goal’ can help to push you in working-less-mode-and-enjoy-life-more.


When I feel what you described, I know that it is time to slow down and get back to life :smile:

Otherwise, the irony is on me, that I’m pursuing freedom, without realizing I already have quite a bit and that time passes (see Living the life).

Many people (including Montaigne, but also people like Zelinski) mention that “hard to focus on other areas” phenomenon; if you focus intensely on one part of your life, it will kind of suck the energy/willingness to do something interesting in other areas.

The red line is quite simple in theory but not always easy to keep: if I feel sad, tired, unhappy, overly concerned about business for more than a week or so, I know it’s time to take more time for myself and things of life (going outdoor, seeing friends, cooking, sex, reading good books, yoga, watching animes, whatever).

It’s good to be disciplined and to move forward in your business. But at the same time, for me the same discipline must apply for self-care, family and other areas :slight_smile:

So well - you’re definitely not alone, I feel this is definitely a bootstrapper thing!


Thanks for that article, I’m gonna check that out. The Joy of Not Working also looks interesting.

if you focus intensely on one part of your life, it will kind of suck the energy/willingness to do something interesting in other areas.

Ya exactly. I feel like I’ve been overworking for the past 2 years and in that time other areas of your life being to atrophy. So it actually takes work to build back up non-work habits and hobbies and stuff. Kind of ridiculous but it’s just like that.

I feel this is definitely a bootstrapper thing

Ya and the interesting thing is that it’s kind of a paradox for us. For most people, it’s just accepted that they’re going to spend all their time overworking. But for us that are bootstrappers, we’re doing it specifically to have freedom. Otherwise we’d be working 80 hours a week at a startup or in finance or something to make a lot of money.

But it surprises me that even for the most successful among us, the ones who really can do what they want - they end up just working. Kinda nuts.

But you’re right it takes discipline. Speaking of which, time to go and get outside for a bit :smile:

Just read that living the life article. It totally nails it. So good. Thanks again for that.

Yes. I can identify with all the above. When things are going well you want to make the most of it. When things aren’t going so well you want to improve the situation. So you end up working a lot. Even when you don’t really need to. It is a struggle to get the balance right sometimes.

I sometimes think of Walter White looking at his huge pile of money towards the end of ‘breaking bad’.

I am taking a month off to travel with my family soon. I don’t want to end up as Walter White. ;0)


I loved how you nailed it! You will be quoted again.

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Me neither, but I loved that money mattress!!

Yes, the amount of pressure in bootstrapping is considerable. @Andy nails it in that in the beginning and slow business times you’re stressed about making enough and then when it’s going well you’re stressed about keeping it going :smile:

Also, as bootstrapping tends to take a long time and isn’t a 6 month hit or miss kinda thing real life builds on the stress. You have a kids for instance. The business goes well and you add employees and their families to the mix and all the sudden your little business with a few people supports 20 humans and you feel that pressure.

I’ve been trying to work on a lot of this stuff lately with mixed results. I wish I had started earlier thinking about it vs just always pushing through working. I do think there’s a big part based on your inherent personality. Some people are better at making time or not letting stress get to them than others are.

I know Jesse Mecham (YNAB) talked about this I think at Bacon Biz, but most founders really should have a therapist or someone they talk to on a regular basis. I think it would have really helped me to have someone like that very early on in the business who can help you stay focused on the broader picture vs always being down in the business.

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Thanks guys - awesome to get feedback from @Andy and @ian.

Ian, I can see how adding employees automatically takes you to a new level of ongoing stress.

Andy, I know you’ve talked about how you’ve avoided bringing on employees for basically exactly this reason. That’s my plan as well. Although you seem to be one of the rare ones that actually sticks to this plan :slight_smile:

The vacation sounds awesome!

I could possibly make more money if I took people on and I do things faster. But I think it would be more stressful and I would end up doing more of the stuff I don’t like doing and less of the stuff I do like doing.

I will still have to work an hour or two a day on holiday doing support. But that’s fine.

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Small price to pay. I’m kind of curious how many hours you work on a regular day if you don’t mind sharing.

Andy - you’re doing much better than I suspected :wink:

I’ve never formally tracked it. And it varies a lot. Currently I am working hard on developing and marketing Hyper Plan, while also keeping PerfectTablePlan going. Which is quite tough. It also depends whether you include things like reading this forum or thinking about Hyper Plan in the bath. ;0)

Probably 30-50 hours per week, most weeks. Sometime more. Maybe 10 hours a week on holiday.

I worked harder when I started bootstrapping.

But then I used work pretty hard when I had a salaried job.

I would take more holiday. But that isn’t really practical with an 8 year old in school.

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My pile is a lot smaller than Walter White’s pile. But I get to sleep soundly at night. :smile:

I write from a hotel room in Myanmar, on a Saturday morning. I should be out looking at ancient Buddhist temples, but instead I’m doing my daily customer support routine.

When self-employed, it takes discipline to start working each day. It takes discipline to stop, too.


Well said.

I’d be curious to know how many hours you typically out in on regular days vs travel days.

That’s a good point. I’ll have to remember that.