The smart thing to do when you feel stupid – and how to get help that’s actually helpful!


This week, I’ve been feeling particularly uneasy.

On Monday I woke up feeling amazing, like I could do anything. But by the end of the day on Tuesday, I felt like a total fraud.

So I called one of my best friends to check in.

“Stein, I feel like I’m all over the place. One minute, I know exactly what I’m doing. And the next, I feel completely out of my league, like a total amateur – silly for even trying to start and run my own business.” 

“Ugh I can relate to that,” she said.  “I feel like I operate at two speeds – either I’m amazing OR I’m the worst. There’s hardly a middle ground. But at least you’re honest about that. You don’t pretend to be perfect or have it all figured it out. You’re confident in what you’re good at and insecure about what you don’t know – everyone can relate to that.” 

She’s right. (And the best).

It’s easy to feel solid in what you’re good at and it’s uncomfortable to feel insecure about the things you’re not good at (yet!). But like Stein reminded me: Be honest with yourself about that. It’s the first step to getting the support you need. No one is the best at everything, it’s ok to admit that you suck at something, which is why you reach out to others for help.

So I called up a business advisor – hoping she could help me suck a little less at organizing my finances to hire someone. 

And here’s where my convo with Stein got juicy:

“It’s funny, I have no issues asking for help,” I said. “I’ve been reaching out to people left and right who know way more about the areas of my business I’m still figuring out than I do. But I’ve had a few calls recently where the point of the conversation was for them to help me get clearer on things, and instead I got off the phone feeling more confused and overwhelmed than before. Just yesterday, I was on the phone with this business advisor who kept using phrases I’d never heard before. I was too embarrassed to have her back up and define terms she assumed I knew, so she just kept talking and I eventually tuned out. The whole thing was a giant waste of time.”

“Yeah” Stein said. “Because it’s not just about asking for help. You also have to stop people and admit when you’re not following them. Otherwise, you’ll always feel like sh*t! Especially when you’re paying someone to help you figure this out – it’s their job to make it make sense to you. Otherwise, what’s the point?”

She’s right. Which brings me back to to you:

My guess is you’re like me and you don’t necessarily struggle to ask for help. You struggle once you’ve asked for help, but the help doesn’t feel like help, it feels like more stress. Right?

And then you’re back at square one needing more help and feeling just as overwhelmed as when you sought the help out in the first place.

It sounds obvious, but if you’re gonna go out on a limb and ask for help, make sure you’re clear about what help actually means to you ahead of time, so that you can communicate that at any moment – and not feel like an idiot for slowing them down or clarifying the support you need. It’s the pro thing to do. (And you’re a pro!)

Next time the person who’s trying to help you starts going too fast, isn’t making sense to you, or just isn’t being helpful in the way you hoped, speak up!

You might say something like:

  • Can you back up a second? What did you mean by X? Not sure I totally understand what that means yet.
  • I’m not totally clear on what you mean by X, but I want to understand. Can you say explain that again? Maybe in a different way?
  • Hey, I know you’re trying to help and I really appreciate it, truth is, what I really need help with is…. 
  • I want to be able to do XYZ on my own… could you walk me through how I’d do that? 

Bottom line: It’s ok to feel dumb sometimes. We’re not meant to be good at everything or figure it all out on our own. But the smart thing to do when you feel stupid is to admit that (in this area!) you are in fact stupid. Be clear about what help actually means to you and speak up when you’re not getting it – because that’s the smart, pro thing to do. 


Big Happy Birthday shout out to my beautiful, wise friend Sarah Stein. I love you so much. I’m really glad you exist. Thanks for being exactly who you are.

All my love,

p.s. If you want more tips on how to speak up with confidence and ask for what you need, grab our free resources from the sidebar! You’ll get instant access and E-Tribe weekly tips/giveaways we don’t share anywhere else.

Read this next…

How to Exude Authentic Confidence and Convey Your Expertise When It Matters Most

Do you ever get frustrated when you find yourself not speaking up in meetings or missing opportunities due to fear of not saying the…

How to Stop Rambling – Fewer Words, More Impact!

Whether you’re in a job interview or pitching a strategy to a new client, try giving them your BLUF. How to give your BLUF…

Oh Baby! Hello From The Other Side…

Some goodies to tie you over while I’m out on maternity leave Guess what? On October 14th, my husband, daughter and I took the…