I’ve noticed a set of related issues that kept coming up in sessions with clients. So, I’m writing about them for others who struggle with the same topics. This one is my heartfelt rant to all of the caring people trying to improve the world who are burdened with the persistent, negative feeling of never doing enough. 

Lily always waits until the last minute before the deadline and then feels terrible that she produced a crappy piece of work. She feels guilty when she’s procrastinating, but repeatedly fails to start early enough to do a good job. 

Paul thinks he should produce a blog post each week, but settles for one a month. Yet, he often misses his deadline and feels guilty that he can’t manage even this small goal. He dreads starting the next post. 

Norann sees her coworker easily completing tasks that Norann struggles with, and feels anxious that she’s not good enough. She has to force herself to work but still never feels like her projects are good enough. 

These people all have one thing in common - they feel guilty that they aren’t doing enough. But doing work doesn’t make them feel better. Doing work just makes them think about the fact they are failing to meet their goals. 

The default way to escape that cycle is to not think about work. This leads to distraction and psuedowork feeling better in the moment. 

It’s common to procrastinate because the immediate pain of starting work outweighs the pain of procrastinating in the hyperbolic-discounting agents we call brains. While that is an important problem I’ll talk about in a different post, it’s not what I’m talking about here. 

Here, work doesn’t feel good even after getting past that hurdle. Lily, Paul, and Norann don’t feel proud when they’ve finished their work because they never feel like it’s enough. Because of that, working doesn’t provide an emotional reward. 

Instead, they feel a constant expectation of failure. This feeling can be subconscious, a vague unhappiness when they think of starting work. Or it can be big, a feeling of trapped doom that nothing they do will really matter in the end. 

Either way, that guilt comes from broken expectations of what they “should” be able to do. 

We are not yet gods. We can’t change ourselves with a snap. If you’re setting yourself unrealistic goals, then repeated failure is around the corner. If you don't take pride in your work because it’s easy for someone else (or if you think it couldn’t have been that hard because you could do it), then you won’t feel the thrill of succeeding at a challenge no matter how hard you work. 

If you aren’t currently capable of meeting the expectations you have for yourself, that’s a fact. Denying it doesn’t make you more capable. “What is true is already so. Owning up to it doesn't make it worse.” Accept where you are, and figure out how to move toward your goal from that starting point. 

You can wish that past you learned skills to put you in a better spot now. You can make plans for becoming better. You can aspire to grow tomorrow into a better version of you. 

You don’t need to feel guilty, ashamed, or worthless about where you are now. 

First, you are worthy as a person regardless of the measure of your ability to make the world better. The world is on fire, and some of us only have buckets big enough to take care of ourselves. If that’s you, you are still okay. 

I’m not saying ability to make an impact doesn’t matter. I really, really care about the world becoming better, and it makes total sense if you want to be in a place to help make that happen. 

But you do not need to feel guilty that you are not there yet. 

It’s common to feel resistance to that statement. Because guilt is what you “should” feel when you failed to do something. More importantly, it feels like guilt is what will motivate you to do better. It can feel like you need to feel bad if you are going to change. 

I’m not saying that guilt never works. Feeling bad that you aren’t doing more can be motivating. But guilt motivation is a double-edged sword. 

You can’t do your best if guilt makes you flinch away from your work. The more effort you need to put into motivating yourself to face work, the less effort you have available to do good work. Even work you would enjoy can feel bad if you feel guilty for not doing enough. If you can’t think about your work without an ugh feeling, then you can’t be your best at your job. It’s that simple, and that hard.

If you’re still feeling resistance, maybe try reading the Replacing Guilt blog series by Nate Soares. There are so many other things that can motivate you besides guilt! 

Think of your feeling of motivation as a system of brakes and gas pedals. Basically, positive emotions move you toward some action, and negative emotions push you away. 

Loving your work is a gas pedal. Caring about improving the world is a gas pedal.

Feeling guilt when you think of your work is a brake. It’s a negative nudge in your mind pushing you away. And that guilt slows you down. So stop spending your finite effort and attention on what you “should” be capable of. Stop docking yourself points for your distance to perfection. 

Because really, letting go of that guilt isn’t permission not to make progress. It’s permission to be proud of the progress you make.

Measure your success against how you did yesterday. You are growing, and that’s what matters. Push yourself as fast as you can sustainably in the right direction. The faster your rate of improvement the better, and some people should be pushing themselves more. But this is a marathon. Burning out is way worse than slow and steady. So emphasize steady, compounding incremental improvement. 

Then let go of that ugh feeling of not being good enough.

It doesn’t matter if you think you “could” have been better now. Remember “coulds” are broken. It doesn’t even matter if someone else is better. Comparisons matter when you’re deciding whether you’re the best person to take on a job or if you are likely to succeed if you continue down a path. Otherwise, all that matters is being the best you can be.  

This is often hard to accept if you’re objectively failing some benchmark. It feels demoralizing if your performance review wasn’t up to scratch, or if you failed again to get the job offer. That pain may be an indicator you should try a new strategy or aim for a different goal. Great, that’s valuable information. 

But even if you’re starting from a place you’re not happy with, you can still be proud of the progress you make right now. Measure your progress, instead of judging yourself against a mirage of expectations. 

And yes, this might take some practice. 

If you never feel like you get anything done, try tracking what you get done each week so that you can more accurately recognize your accomplishments. Check if your expectations are consistently wildly greater than what you actually accomplish. If they are, work on your calibration. Because sometimes it’s easy to dismiss what you’ve already done as trivial, despite how hard it actually was. Compare how easy your success feels now to how hard it felt before you did it. 

If you think you can never get enough done, ask yourself what “enough” would look like. Would what make you feel happy with your day? Have you reached that “enough” in the past week? If not, your sense of enough is broken. Expectations should be calibrated against what you actually do. Your realistic “enough” should be something you can meet at least half the time. 

“Enough” isn’t what you’re aiming for, of course. You want to have those peak days where you get way more done than normal. But think about it, those days are defined by being better than normal. It’s literally impossible to have a better-than-average day every day. So, yes, aim and optimize for peak days. It’s okay to reserve excitement for those days you do more than you normally can. But you don’t have to feel like a failure every time you fall short of that goal. It’s good to be content with a solid day’s work. 

Furthermore, your sense of enough will move as you expand what you can do. Remember that you have time to grow. Consider what you can do in a year, not just a day or a week. 

When you notice yourself being upset with your progress or feeling guilty for not doing more, ask yourself if you’re doing better than you did last year. If the answer is yes, remind yourself to celebrate that accomplishment! 

If this is really hard for you -- if you struggle to feel pride in an above-average day of work -- I encourage you to read the blog Minding Our Way by Nate Soares, the book Gifts of Imperfection by Brene Brown, or consider talking to a therapist. (I’ve benefited from all three over the years.)

Because feeling constantly guilty for not doing enough will sabotage your efforts to succeed at your goals, let alone learning to love your work. So let that guilt go. Build up your motivation to propel you forward without this brake. Then go slay your goals. 

Acknowledgments: Many thanks to Neel Nanda for his feedback on post.