The Feedback Gap: The Loneliest Part of Working for Yourself
How to stay grounded when no one is telling you you’re doing a good job.
A few years into working for myself, I came up with what I still think is my best business idea ever: a daily compliment generator. You put in a few details about yourself, hit the roulette wheel, and voilà! One specific, unique compliment to power you through the day.
It was both a funny bit and a painfully accurate diagnosis of what was happening in my work life: I was starved for feedback.
When I worked at a big management consulting firm, every project came with a side of performance review. Detailed anecdotes, numerical ratings, bullet-pointed lists of achievements, and a neat summary of everything I did well. Then I moved to a startup full of ex-consultants. Still structured, still validating, still little hits of “you’re doing great, keep going.”
And then… I went out on my own.
And, nobody told me I was doing a good job.
Nobody told me I was doing a bad job either.
It was just… silence.
I kept thinking: Okay, maybe if I work a little harder… maybe if I add one more thing… maybe if I respond a little faster… maybe then someone will tell me I’m doing a good job. That moment doesn’t come. Not because you’re not doing well, but because in self-employment, there is no built-in feedback loop.
Sure, the feedback eventually shows up in the form of new clients, referrals, repeat business. But day-to-day? You’re flying without instruments.
Until you build them.
The thing that blindsides a lot of independent workers
People talk about how working for yourself requires discipline, grit, comfort with uncertainty. But nobody warned me that if you’re coming from a full-time job into entrepreneurship, you will go from getting regular feedback to getting…. almost none. Instantly.
And when the feedback stops, the brain goes hunting for signals:
Am I doing enough?
Am I doing it right?
Does anyone notice?
Does any of this matter?
And when your brain doesn’t get signals, it starts… improvising. That’s where things get messy.
The Pitfalls of the Feedback Gap
1. The Assumption Trap
Instead of receiving feedback, you imagine it. You leave a client meeting and replay it in your head:
“She didn’t smile at slide 7. That’s bad.”
“They said ‘we’ll review and get back to you.’ That means they hated it.”
“No exclamation point in the email. Ugh, this one’s not going to come through.”
Without a coworker in the meeting to gutcheck you, or tell you what you did well or offer a second opinion of a conversation, you are left to make your own assumptions about how things went. And most of us assume the worst possible interpretation.
The shift:
Ask instead of assume.
“How does this direction land for you?”
“Anything missing?”
“What would you like more of next time?”
Clarity feels (super) awkward for 2 seconds and saves 2 weeks of spiraling.
2. Borrowing Validation From Loved Ones
The moment I realized what an impact the feedback gap was really having on me? When my husband called out how annoying it was that I was always asking him for “one specific, unique compliment.” (See: business idea above.) When work hadn’t given me any gold stars that week, I turned to him as my performance review committee.
He didn’t need to (and really shouldn’t) carry that weight.
And I didn’t actually want my sense of competence to live inside my marriage.
The shift:
Partners can support you without being your primary source of professional validation. Find professional reflection in professional places.
3. The Anxiety Spiral
The silence → assumptions → anxiety loop is so real.
When we started talking about this, Kaylin immediately ticked off several examples of client conversations she’s been spiraling in this week:
Proposal not answered in 24 hours = I quoted it too expensive and this project will never get to yes
Email takes a week to reply = they think I did a bad job are are disappointed in my work
Curt Slack response = I said something wrong
Meanwhile the truth 99.9% of the time = they’re busy, traveling, sick, parenting, have too many emails in their inbox, or forgot.
The shift:
Interrupt the story.
Ask yourself: What is actually known?
Usually… nothing other than “they haven’t replied yet.”
Okay, but what’s the fix?
Self-employment does not magically get easier. We just get better equipped (and if you’re reading this, that’s exactly what we’re doing here together at The New HQ.)
And the difference between “spiraling in silence” and feeling steady and grounded isn’t luck or personality. It’s building systems, finding tools, and connecting with community that replace the feedback loops you used to take for granted.
Here’s what has actually helped me, not hypothetically, but in real life, in the trenches.
1. Build feedback into the work
Most clients give feedback only at the very end of a project, right when you’re emotionally spent, and trying to decide if it’s a good thing or a bad thing that the project is wrapping up.
When Kaylin delivers leadership trainings, she offers the motto: “solicit feedback early and often.” The more accustomed you are to giving and receiving feedback throughout the process, the more opportunity you have to innovate and grow (and avoid silent spirals).
Just as she taught me to not wait until the finish line and instead build in opportunities to gather testimonials throughout the project, she taught me to build in a few micro-feedback checkpoints into my work:
5-minute midpoint pulse check: “What’s working? What do you want more or less of?”
After deliverables #1 + #2: “Anything you’d tweak before I keep going?”
Weekly 3-bullet update: “Here’s what I did, here’s what I’m doing next, here’s what I need from you.”
Clients love it because it makes them feel heard and taken care of. I love it because it stops my brain from writing fiction in the silence.
This isn’t about insecurity. It’s about alignment.
2. The Weekly Self-Review
My sister, Erin, inspired me to set aside a few minutes every Friday to journal. I modified The New HQ monthly success check-in down to 3 really easy-to-answer questions:
One moment I felt great about work this week…
One thing I’m proud of this week that no one saw…
One thing I learned about how I work this week…
The point is to celebrate the wins you are proud of, not what someone else told you (or… didn’t tell you) went well. A good self-review creates internal reinforcement, which matters when nobody else is handing out gold stars.
3. The Kudos Folder
Whenever someone (a client, a contractor, a collaborator) says anything kind about my work, I tag it Kudos in my inbox. I don’t format it, I truly just take screenshots of Slack messages or LinkedIn messages and don’t add context.
On the days when nothing feels like it’s working, I’m questioning my value, a client hasn’t replied in 48 hours and my brain is writing a novel about it
…I open that folder.
It is fully stocked with proof that I am competent, impactful, and appreciated, and completely turns my day around when my nervous system has forgotten that.
4. Chosen Colleagues
We talk a lot at The New HQ about building a circle of chosen colleagues, because working independently is amazing, but working alone sucks.
Chosen colleagues are the stand-ins for coworkers we no longer have. The people who know how you operate, have seen enough of your patterns to spot what’s really going on, and can help you process even though they weren’t in the situation with you.
They’re close enough to understand the context, but removed enough to offer perspective.
One of the things we miss most about working in an office is having someone to Slack the second something hard happens and have them immediately respond: “Ugh, that freaking sucks.” before saying “Okay, what do you want to do about it?”
That “being seen first” moment is powerful. It regulates your nervous system so you can actually think clearly.
Chosen colleagues are the closest shortcut we’ve found to recreating that when you work for yourself.
5. AI as a reflection tool
If you call all your chosen colleagues, and they’re not available in that moment, open up your most-used AI tool. This sounds a bit silly, but it works.
I ask my AI notetaker (Granola! If you haven’t started using it, you can thank us later) or ChatGPT questions like:
“What did I do well this week?”
“What are opportunities for improvement without self-criticism?”
“What patterns do you see in my work lately?”
It’s not praise. Okay, fine, maybe a little bit but more importantly:
It’s perspective. And sometimes perspective is more regulating than praise.
It gives you the emotional regulation that a performance review used to give you, without outsourcing your identity to feedback you may or may not receive.
What I’ve learned
For a long time, I feared that my need for feedback was about needing ego strokes. Not true.
When structured well, soliciting feedback is about:
staying connected to your impact
reducing unnecessary anxiety
catching good patterns and bad patterns early
remembering you’re a whole, competent adult running a business, not a student waiting for a grade
Self-employment isn’t a vow to never need affirmation again. It’s a vow to stop waiting for someone else to hand it to you.
I used to think the goal was: replace external feedback with internal feedback.
But I’ve realized that self-employment is learning to hold two truths at the same time: I am doing a great job. And I can keep getting better.
Recognition is not childish. Validation is not weakness. Affirmation is fuel, and fuel keeps you in the game.
So if you’re building quietly, without applause, we see you.
And you’re doing an amazing job! You’re figuring out something hard.
And you’re farther along than you think.
Another great one. Thanks, you two.