

In This Edition…
9 to 5 Dilemma: Dream Jobs DO Exist.
Coach’s Confession.
Events & Releases… Coaching Club is Open!
Let’s Get Social.
Dollyism.
For those in a rush, the TL;DR:
A reader pushed back on the "no dream jobs" line and made me rethink the language. The truth: dream jobs are a corporate invention designed to make your work responsible for your worth. Right-fit roles at right-fit moments are the real thing and you build them by naming the life first, then finding the work that funds it.
Also this week, the four times I almost quit this year, and what each one taught me. Spoiler: the advice I keep giving you is the advice I keep giving myself.
Plus: come find me on Instagram and TikTok. I'm doing the messy middle in public on purpose.
And now for the long form content fans…
First of all, CONGRATULATIONS! You deserve a role that supports your life, your goals, and respects your contributions. In this market, those roles are hard to come by!

You did something some people never do. You made deliberate choices, made the right moves at the right moments, and you ended up in a role that fits you. The leadership, the team, the work that matters, the Sundays that feel like Sundays again… none of that is an accident.
I want to tell you what I think you actually found, because I think it's bigger than a dream job and I think the language matters for the readers who haven't gotten there yet.
The phrase dream job was built to make us tie our worth, our identity, and our happiness to work. It's a sticky phrase.
It makes the job responsible for things a job was never meant to carry. It makes a layoff feel like a referendum on who you are.
It makes a bad quarter feel personal.
And every reader who hears the phrase wonders why they haven't found theirs.
What you found is something I want to give a better name to. It's a right-fit role at a right-fit moment. A role that fits the life you already wanted with the team you respect, the work you care about, the Sundays you get to keep.
The dreams are not the job.
The dreams are the life.
The job is what makes the life possible.
And you, my friend, figured that out before most people do.
The four moves:
Name the life before you name the job. You did this without realizing it. Most readers haven't yet.
The question to start with isn't what's my dream job.
It's:
What do I want a Wednesday evening to look like?
What do I want my body to feel like at 6pm?
What do I want to be known for outside of work?
The job's job is to fund those answers. When you start there, the right role gets a lot easier to recognize.
The language we use about work shapes how much of us it gets. Try this on for size:
"It's a role that fits the life I'm trying to live. The work is meaningful, my team is strong, and the pace is sustainable.”
That's a sentence that honors what you built without handing the job more than it can hold.
Notice what's missing… the cosmic framing, the implication that you've arrived, the suggestion that your worth and the role are now the same thing. They're not. You're you. The job is the job.
Right-fit roles at right-fit moments don't stay that way forever and that's okay. Companies change. You change. The life you're building now will look different in ten years. The healthiest thing you can do is hold this role with appreciation and a light grip. Love what it is now. Don't ask it to be the answer forever.
For the readers who aren't here yet — the work is the same. Stop asking what is my dream job. Start asking what is the life I am trying to build, and what kind of work would fund it well. The first question keeps you chasing. The second one lets you choose.
You found something better than a dream job in a role that fits the life you wanted, built by you, on purpose. That is rarer, harder, and more meaningful than what most of us were told to look for.
The dream is the Sunday that feels like a Sunday. The dream is the team you'd run through a wall for. The dream is the version of you that exists outside of work and gets to come home to herself at the end of the day.
The job is what makes it possible.
Build the life first. Then go find the work that fits it.
Thank you for writing in. You gave me something to think about more deeply in a new way!

Have you checked out gumption. Coaching Club Yet?

The Advice I Need to Hear.
The longer I've been working for myself, the more I've realized something I didn't expect.
The best coaches coach to the advice they've needed themselves.
There’s perception that coaches do this work because we've figured it out. That we're standing on the other side of the hard thing, hand outstretched, ready to pull you across.
I used to think that's what I was supposed to be, too. The expert. The one who had the answers nailed down before she opened her mouth.
That isn't what it is at all, actually, not for me at least.
It’s actually humility.
The work I do with clients is the work I've done on myself, often three months ago, sometimes still in progress. I am not on the other side. I am one step ahead at best, and on a hard day, I'm right next to you doing the same thing.
Here is what that has looked like for me this past year and what I had to learn from each one of them.
The newsletter I almost stopped.
I considered stopping Cup of Ambition because it’s been so slow to grow an audience. Why am I not immediately at the pinnacle of my writing success after a year of consistency!? 😂
Even though more than 75% of you read every single issue.
Even though I get notes from readers every other week telling me that something I wrote landed with them and they still think about it.
I almost stopped because the number on the dashboard wasn't big enough to make me feel like I deserved to keep going.
Here is what I had to learn.
A room of anyone, no matter the size, is a room of people who care enough to read and listen. The metric I was using to make myself feel small was the wrong metric. The right metric was the open rate and the open rate was telling me the truth that the subscriber count couldn't.
The advice: if the number you are using to measure your worth makes you feel smaller than the evidence does, you are using the wrong number.
Find the metric that tells you what is actually happening. Use that one.
The business I almost gave up on.
I almost throw in the towel on this whole business regularly because I’m not as popular as the people doing this work with hundreds of thousands of followers.
I’ve watched coaches with worse advice and better lighting get five times the engagement I do. Wondered if the problem was me.
Here is what I had to learn.
The coaches with the best editing are not always the ones with the best thinking. Some of them are excellent. Some of them are selling a kind of certainty I don't believe in and wouldn't sell if I could.
The question isn't whether I can become them. It's whether I want to. The answer, when I finally let myself answer it honestly, was no.
The advice: the person you are comparing yourself to is doing a different job than you are. The fact that they are louder is not evidence that they are better. The fact that they are more polished is not evidence that they are more successful.
Decide what you are actually trying to build. Stop measuring it against something that was never the goal.
The voice and personality I almost changed.
I second-guess my voice all the time.
“No one takes humor seriously at work.”
“Experts are way more polished.”
“You use too many emojis, Dolly quotes, and other distractions to be seen as credible.”
I wondered if I should soften it, brand it, make it look like everyone else's.
Do people take me seriously? Am I polished enough to be an “expert”?
Here is what I had to learn.
The thing that makes me different from every other career coach on the internet is the same thing I was about to sand off.
The humor is part of the value. The casualness is intentional and it makes people feel comfortable and less intimidated than the stuffy, buttoned up stuff.
If I take that out, I am not more marketable. I am invisible.
There are thousands and thousands of career coaches publishing perfectly fine, perfectly forgettable advice into the void. I do not need to be one more of them.
The advice: the part of your work that feels too much like you is the part that is most worth keeping.
The market is full of people doing a sanded-down version of the thing. There is room for the version that sounds like you. There is not room for one more version that sounds like everyone else.
What I keep telling clients, and finally started telling myself.
Every time I tell a client to stop measuring her worth by the title someone else assigns her, I am also telling myself.
Every time I tell a reader to speak to impact instead of activity, I am also editing my own LinkedIn.
Every time I tell someone in a 1:1 to stop apologizing for the size of her ask, I am rehearsing for my next conversation about my own rates.
The work is recursive. I am not above it. I am inside it.
So here is the thing I wanted to say to you this week.
If you read these issues and assume I have it figured out — I don't. I have a practice. I show up. I write the next one. I send it to people who I am profoundly grateful for. Some weeks I almost don't. Some weeks I write the issue because I almost didn't.
The work is the work. And the advice I am giving you is, more often than not, the advice I am giving myself.
Let’s Get Social.
If you follow me on LinkedIn, you're probably used to seeing me in your feed daily. That's where my day-to-day thinking lives… the stuff that doesn't make it into the newsletter because it's faster, looser, and meant to land in the middle of your workday.
Instagram and TikTok are newer. I recently decided to take my own advice and actually start building my brand there, too.

I’m challenging myself to learn, accept the embarrassment of not immediately being the best at something, and allowing myself to just let it be as it is (ahem, are you sensing a theme in this edition? 😂)
I'm playing around with it all. Figuring out what feels like me and what doesn't. What's funny. What's helpful. What lands and what falls completely flat.

So this is less of a "follow me" and more of an invitation. Come watch the experiment. Tell me what you think. Send me a DM if a Reel made you laugh or something you saved because it was interesting.
I’d love your feedback!
Instagram (@get.gumption.careers)
TikTok (@get.gumption)
Dollyism.

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