In the comments for my previous post, two totally different people asked me what appears to be the exact same question:

Josh Brown comments

“How’d you get past that initial period when you weren’t making any money? How’d you stay motivated?”READER #1

“And how did you find the ‘grit’ to keep going during the early days?”READER #2

This comes as no surprise to me, because I’ve been teaching my students how to bootstrap a product for ages now, and people fail in predictable ways. This right here? One of the most fundamental difficulties of bootstrapping — hell, one of the most fundamental difficulties of all human endeavor, period.

How do you keep going?

It’s a question that begs for a list of tactics. But I’m not going to give you any — not yet.

Because the question is wrong

These two readers didn’t actually ask, “How do you keep going?”

Reader #1 actually asked “How do you stay motivated?” — which isn’t a question of action, but of feelings.

And Reader #2 asked, “How do you find the ‘grit’?” — which isn’t obviously about feelings, but is about some…quality…that is out there, somewhere, waiting to be found.

The Grit Is Out There meme

This premise makes for good TV, but it doesn’t make for a good life.

1: Why motivation won’t take you anywhere.

We all know what “motivation” feels like… but what is it, exactly? Well, it’s trite to talk dictionary definitions, but in this case it’s really interesting: Motivation comes from motivus, a Latin word that means literally “to move.”

Bam! We talk about motivation because it’s something that sets us in motion.

But…motivated isn’t a state of being, it’s a feeling. As any poet, lover, or parent knows, you can’t capture a feeling and hold it in a jar forever. No matter how motivated you are to do so. Feelings are fleeting. They slip through your fingers when you try to hold on. They’re unpredictable.

Feelings are like weather in your mind: Sometimes it’s sunny, sometimes it’s cloudy, and sometimes it rains, and sometimes that means something, and other times it means nothing.

Sometimes you feel motivated and then you do things. Sometimes you feel motivated and do nothing. But most of the time you don’t feel particularly motivated…and you still do things:

You don’t only feed your pets or kids when you feel like it. You don’t only show up for your loved ones when you feel like it. You don’t only do your current job (whatever it is) when you feel like it. Do you?

Then why would you set up your brand new baby business to live or die based on what side of the bed you woke up that morning, or how much starch you ate at lunch, or what kinds of emails are in your inbox?

How to stay motivated Google Search

Don’t buy my explanation? Well, try this sentence on for size: “Oh, it’s raining. Guess I’m not gonna feed my cats today.” Ludicrous, right? Well, it’s no different than “I don’t feel motivated. Guess I’m not going to feed my business today.”

If you love your cats, or your business, you’ll do what you have to do to ensure their survival, regardless of how you feel in the moment.

Waiting for “motivation” to move your butt is just a clever way to avoid taking responsibility. Full stop.

2: Why you can never find grit.

Likewise, grit may be the subject of the latest pop psychology research, but that research isn’t about an innate quality, but what people do. It may be called Grit (personality trait) on Wikipedia, but the scientist who popularized the term describes it as “sticking with things over the very long term until you master them.”

Ladies and gentlemen, that’s not a trait — that’s a behavior. You can know “grit” by what a person does, not what they have. Can you “find” a behavior? No. You can only do it.

So, now, with that out of the way, let’s talk techniques. What do assha—pardon me, thought leaders usually say about staying motivated?

Some combination of…

  1. Read inspiring things.
  2. Talk with with people who inspire you.
  3. Post reminders somewhere you can see them, like inspirational photos.
  4. Two words: Vision Board. (*barf*)

Now you can probably see the issue with this list, right?

These steps are all trying to manage a feeling — an internal state — and nothing about action whatsoever.

And you don’t need them.

You know perfectly well how to achieve without motivation or grit

Your kids or pets don’t starve when you’re having a bad day. You’ve got some source of income now — you haven’t been fired for just, you know, not showing up. You have friends and family who know they can count on you.

If you can manage these things, you already know how to work on your fledgling business even when it’s not making any money. So you can keep working even when it does.

SIDEBAR: Yep, it’s exciting when you start making money, and that alone can be motivating. But trust me — the high doesn’t last (thanks, hedonic adaptation!). So you have to learn to work without motivation, without money, to ever make it to making money regularly (so that making money actually becomes boring and therefore unmotivating again).

How do you keep going? You keep going.

It’s that simple: How do you keep doing something? You keep doing it. You show up. You do it.

So…what works for you, in the total absence of motivation? You know best. Chances are very good it involves structure — you feed your kids or pets several times a day, and you go to work every day, or whatever works for you.

What we did before our business was making money

We kept it pretty simple, really:

What we did was to work every Friday (and many Saturdays) on Freckle until it shipped, and then more often.

And yes, I made plenty of mistakes while we built our business on the side. There were months when I (foolishly) overworked myself, or committed too much to the consulting side of our business. At the worst, we let Freckle languish entirely for 2-3 months (twice). It hurt our business, for sure, but not as much as it could have. I’m not ashamed to tell this story because of what we did next:

We rolled up our sleeves, and fixed all the things we let go, including the embarrassing 2-month-old support emails we had to answer with apologies.

It took us 2 years to reach $15,000 a month in recurring revenue ($180,000/yr). In that long term approach, those few missing months — and the pain of feeling so embarrassed over them — were nothing.

What I’ve learned from experience is that manipulating feelings is a fool’s game.

Creating habits and setting up structures is the only way you can achieve long-term goals.

And that un-sexy but smart approach comes with an added bonus: Motivation, like many feelings, comes much more reliably after you take action, rather than before.

Help! How do I create good habits?

My top recommended resources:

  1. The Power of Habit (Amazon) — watch this video I made about it
  2. Tiny Habits.

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