How to deal with the feeling that you’re not doing enough

If you’ve ever struggled with the feeling that you’re not doing enough, or being good enough, you’re not alone. I feel you. I’ve been there too.

Here are three things that have helped me in these situations. I am by no means perfect and I also get bouts of doubts, negativity and self-judgement. When that happens, I often turn to one of these strategies.

If you’re not in the mood for reading right now, you can simply skip to the end for the summary. Go ahead, I won’t judge ๐Ÿ˜‰

Now let’s dive in to the first strategy which to measure the gain and not the gap.

The gap and the gain

Dan Sullivan talks about the difference between the gap and the gain. He points out that you can measure progress in two ways. Either focusing on the gap between where you are and where you want to be, or the gain between where you were before to where you’ve come today.

Guess which version feeds the “not enough”-monster?

To help you focus on the gain, keep track of where you came from and your milestones along the way.

One way to do that is to create a Jar of Awesome (a name I tried to track down the origin of, and I believe it is Tim Ferriss. Please correct me if I’m wrong). This is a place where you continuously add good things every time they happen, but also bad things.

This helps to take the sting off of the negatives, because often when you read them afterwards they have lost their significance. But more importantly, the Jar of Awesome is there to remind you of all your positives and accomplishments. You have something to help you focus on the gain rather than the gap.

The irony here is that the brain is a master pattern matcher, and it brings your awareness and attention to the things that stand out. It also has a preference to focus on threats and negatives, since that is how we’re wired in order to survive.

This means that as you start to do awesome stuff, it will start to become business as usual and the brain begins to put less weight on it.

The more you excel, the less novel it will be, and your brain will steer your attention away from it and towards the negative stuff.

Your Jar of Awesome is your counter-measure against that natural tendency.

It can take many shapes and forms.

I have a friend who keeps a gmail folder called “yay me” where she files all positive comments and compliments she receives. Other names and similar ideas I’ve encountered are collecting a Brag Sheet, or a Smile File.

Use whatever works for you:

  • a digital folder of files and screenshots
  • a Notion page
  • a physical scrapbook
  • your favourite note-taking app

As long as it’s easy to actually go back and look through it!

I personally keep a yearly running text document where I add the good and the bad things that happen to me over the course of the year. I usually add to it during my monthly reviews, and I go over it as part of a retrospection in my quarterly reviews.

Our minds play tricks on us and we easily forget the details. Reading about how I struggled with something months ago that I finally nailed is much better for my self-esteem than only focusing on far off future goals that I still haven’t reached yet.

And that leads us to the second thing which is about finding enough-ness.

When and what is “enough”?

When you have this nagging feeling that you should do more, ask that feeling to quantify what it means. When you have done enough โ€“ how will you know?

Will somebody tell you?
On what authority?

The insidious thing is that even if you get a seemingly straightforward answer like “I have done enough when I do X”, when you finally reach that place the finish line will have moved and there’s always the next thing after that.

What you’re really after is a state, a feeling. Not a place you can objectively measure.

Your discontentment can actually be a blessing in disguise. It shows that you have a desire, that you want to go somewhere. The opposite is depression, where you don’t have any motivation to do anything at all.

I’ve been there too.

If the choice is between having nether motivation or desires or having motivation and unsatisfied desires, I’d go for the latter any day.

Even if it’s only a stepping stone towards an even better emotional place, it’s definitely a step up from the alternative.

It shows that you’re alive inside.

I’m convinced that it’s possible to strive for excellence and still be happy. For me, a key thing was to learn and accept what is “good enough”. I had impossibly high standards of acceptance. Loosening them was scary, but the result wasn’t that the quality of my work plummeted like I feared but instead my sense of happiness and contentment increased.

We want to have a sense of progression

A feeling of not doing enough is often rooted in a need for some kind of sign or validation that you’re on the right path and you’re doing ok.

This is a need that gamification capitalises on. Imagine if Life would give you some kind of badge, or another visible sign of progression as you move along in your journey:

“Achievement unlocked!”
“You have levelled up your character to level 32. Well done!”
“You got the badge ‘Adulthood lvl 5’. There are 6000 points to the next one!”
“You have collected 346 thingamabobs. Trade 200 for a luck booster in the game-of-life shop”

By collecting what Jess Lively calls “shiny pennies” along the way, we try to externalise and make the feeling of progression in life visible. The fancy stuff, the status symbols, the academic credentials or social media followers. Unfortunately, as many rich people can tell you, it doesn’t help in patching the hole of not-enough-ness.

The biggest and most important things in life give you very little visible or tangible feedback. In contrast, the things that are often insignificant in the long run have little dopamine hits of instant gratification built in. The stuff that Khe Hy calls $10/hour and $100/hour work. Hitting inbox zero, crossing off the todo-list of today, or setting up the perfect productivity system in yet another tool.

Either you end up chasing these dopamine hits, which adds to the gamification feeling of life but leave you with that nagging sense that there’s something missing and you’re not really getting anywhere.

Or you try to focus on the bigger impact work, but there’s very little external feedback so it’s hard to navigate and you’re uncertain if you’re doing the right things or if it’s even working at all.

Look for happiness in the doing

The best antidote that I know of is working on finding happiness in the doing, rather than in the achieving. Bringing the attention to the here and now, instead of projecting it towards all the things you could’ve, would’ve, should’ve done instead of โ€“ or in addition to โ€“ what you actually did.

There is always a next thing. There is no end of things to do. The decision that you’re on the right path and that you are ok lies within you.

Your todo list is essentially a facebook feed. At some point of the day, you have to say “ok, that’s a wrap” and go and sit with your amigurumi crocheting or fuse beads pixel art. For some of us, it’s harder than one might think.

For me, I used to live life through the things I did. It was how I assessed my life, and how I measured progression. Done, done, done. Check, check, check. I wasn’t really aware of it at the time, but you could almost say that I was a human doing rather than a human being.

I had to learn to just sit and allow things to be. To explore the inner world and not just the outer world. (Ok so in my case I had no choice as I had a health crash that totally incapacitated me. It gave me quite an identity crisis and I had to figure out who I was now that I no longer could do. I share my lessons because I hope that by doing the work beforehand you can avoid sharing my fate.)

In time, I worked at bringing my being into my doing. The more I was able to do that, the more satisfying it started to become. It also meant that I started to evaluate the things I committed to more by how much I would enjoy doing the work, and less by what others wanted or expected me to do.

This didn’t mean that I gave up on setting goals and having dreams. I still wanted to do the things I wanted to do.

The desire to do things is not the source of the problem. The problem is that you judge yourself over how much (or little) you have done.

Thus we meet the main character in the last section: the inner judge.

The process of the inner judge

When you measure against the gap, you make instant judgements about it. How big that gap is, which size it ought to be etc.

The road to unhappiness here has three components:

  • Expectations. You have an image in your head of how you want things to be, or think they should be. You desire or expect a certain outcome.
  • Evaluation. This is where you asses and compare your current reality with the expected or desired. Essentially measuring the gap. You evaluate your current position, and the inner judge puts a label on the result. “Good” or “bad”.
  • Identification. The final piece in the puzzle is how much you attach this label to your own identity. How much self-value you put in the result of the evaluation. If the result was “bad”, does it trickle down into an evaluation of you as a person as well?

The result of this process gets turned into an inner story that runs on repeat. Uncovering the assumptions behind each step in this process helps to unravel that story and make it lose its power.

Investigate the assumptions you’ve made at each step.

  • What is your standard of acceptance? What are your expectations? Put them in writing. Are they even realistic?
  • How do you evaluate your result compared to those expectations? Can you identify and put a name on the assessment?
  • What does this evaluation mean to you? How important is it to you, and do you attach any meaning of it to yourself as a person?

A dis-attached desire of mastery, evaluating yourself as a beginner still, and seeing the current state as totally ok considering your circumstances will not be a source of unhappiness. Evaluating yourself as bad at something will make you sad only if you allow the judgement to creep into your identity.

Can you make your inner judge unemployed?

This way of not attaching your identity to a negative evaluation is part of the growth mindset. Making mistakes and doing less than stellar work belongs to the learning process.

I’m personally really awful with anything that has to do with balls. Throwing, catching, kicking, hitting. If it moves through the air and I’m supposed to be sender or receiver, I’m either going to drop it or miss altogether.

I used to be very self-conscious about this. I’d rather not show my clumsiness, and I didn’t like the feeling of everybody laughing at me and my misses and mistakes. I avoided any and every opportunity that came my way involving balls. Until I decided to embrace my suckiness.

If I don’t expect myself to be better than I am, I can rest in the knowledge that yes, I am in fact pretty crap at this. I’m still ok as a person.

I even warn people to not expect me to return any throws or kicks, but I’ll happily join the game anyway. Ok, so I will often be the source of some laughs. Let’s make it time for some silliness and entertainment instead. And if I lower everybody’s expectations enough, I’ll actually get some credit and cheers for finally catching that first ball out of 20 shots! Yay me!

Not placing your identity in the evaluation is of course much easier regarding things that matters less to you. It’s when the stakes are high that we really need to do some inner work.

Much of our evaluation of where we are comes from comparing ourselves to others. That’s where tons of hidden expectations creep in. “Look at him, I’ve worked longer than him but he has X and I’m at Y. I should really have X too”.

We forget that we compare our insides to their outsides. It’s never an apples to apples comparison, because we don’t have the same history, skills and circumstances as anybody else. We don’t know the effort, time or sacrifices behind whatever result we see and compare ourselves with.

This is where the process of identifying the three components of judgement come in handy. Pull out that journal and find a quiet space.

After a while, you might start to see a pattern where the same stories and judgements come up again and again. It’ll be easer and easier to identify them “on the go” and nip them in the bud as soon as they start to rear their ugly heads. Or at least become aware of them.

Be patient and give yourself grace

Writing all this up makes it sound pretty easy, when in fact some of these things take time and effort. Changing thought patterns is not done overnight.

Sometimes though, just uncovering and naming a hidden assumption or expectation will make it evaporate. I’m amazed at the number of times I’ve had a nagging unspecified feeling and as soon as I tell my husband about it and can put a name on it, the tension is released and I instantly start to feel better.

Other times, knowing and understanding something intellectually won’t change the underlying emotions and you’ll need to do more inner work. Talking out loud is often even better than writing, so if you have someone close to you with whom you can share these kind of things that would be great.

Don’t be afraid of seeking out a professional either if you’re really stuck. Coach or therapist – they both carry the gift of a space to detangle our inner messes.

Once you start to become more aware of what’s happening while it happens, don’t judge yourself over judging yourself ๐Ÿ™‚

It’s ok. You are ok. We’re all trying to navigate this space together.


Write in your journal, talk to a trusted listener, and be kind to yourself while you’re processing. Patience and self-compassion goes a long way.

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