You're Accomplishing a Lot. So Why Do You Still Feel Behind?

Have you ever felt like you're getting things done, reaching your goals, and other people even look at you and think, "Wow, she's doing so amazingly well," and yet you still feel like you're behind?

That's exactly what I'm sharing...

I see this pattern constantly in the high-achieving women I coach: women who are successful on paper but don't always feel successful. They reach one goal and then almost immediately start focusing on the next one. There's very little time in between to enjoy what they've created before they move the finish line again.

And I've lived this myself.

When Achievement Doesn't Feel Like Enough

I had a very meaningful milestone when we won a podcast award and were ranked in the top 50 podcasters: number 17 out of 50 that year. Rather than saying, "Wow, this is amazing," I was already thinking: How do I get closer to number one? How do I increase my downloads? How do I increase my subscribers and my listen rates?

I didn't even let that accomplishment land.

That's what I see in so many women. Friends of mine who are successful, clients of mine who are successful, women in my CAPS community (Canadian Association of Professional Speakers), so many different places. A lot of times we're either looking at all the things we did wrong, or we're jumping ahead to all the things we want to accomplish next, because we’re ambitious, or the achievement didn't satisfy the itch, or for some reason or another, we think we need to do more.

Many of these women come into coaching or into my circles already accomplishing a lot. They don't need someone to push them harder. They really just need a place to step back and see what they've already built, to get perspective outside the noise. Either the noise in their head of "do more, do better, do the next thing," or the noise of the business and the responsibilities and the clients and everyone else who needs them.

Real Stories of High-Achieving Women Who Felt Behind

The Year I Had a Baby

I can remember going through my Dynamic Year program (now called The Breakthrough) with a couple of other coaches the year after I had my daughter. She would have been about 13 months old. I said to them, "I didn't accomplish much last year."

They said, "Are you kidding me, Diane? You had a baby. You breastfed the baby. You kept the baby alive. You took care of the house. You still ran your business. You made mom friends. You went hiking with them. You brought your daughter to a lot of baby-and-me things. And so much more!"

But I just thought: "Oh, I was going to do that anyway." The process of growing a baby and having a baby didn't feel like a big deal because somehow or another, I would have had the baby. That's what happens. Nine months and the baby comes out. I just thought it was normal. I didn't actually see that as a success because of the hundreds of millions of women who have gone before me and done it.

The Client Who Needed More Certifications

I had a client who had been in business for a long time, and she looked really successful from the outside because she was. But privately, she kept feeling like she needed more training, more certifications. She couldn't run her own workshop until she did more and more things. She kept focusing on what was missing rather than what was working in her business and all of the knowledge she already had.

Through coaching, she started to see that she wasn't actually behind. She started to see how she was already ready to deliver those workshops. She didn't need more certifications to give her permission. She really just needed to give herself permission. She needed to acknowledge her own progress. She needed to decide what she wanted success to look like and feel like going forward. And after she did, she held her first workshop.

The Client Measuring Herself Against Someone Else's Timeline

Another client was newer in her business but kept measuring herself against someone else's timeline, someone else's success. She saw other women growing their businesses faster, launching more, putting out programs, getting their websites done, having beautiful business cards and everything made her feel like everyone else was further ahead.

Being part of a group coaching environment, though, she started to see: "Oh wow, everyone's in a different season, and everyone has a different pace that they run at."

My son is a sprinter. When they asked him to run the 1,500 at track, I was like, "Why? That's not his pace." His friend who runs the 1,500 is not very good at the 100 and vice versa. It depends on the pace you want to go at, and what you're capable of, as to what your output is going to be.

Rather than feeling like she needed to do everything at once, make the website, have all the marketing materials, do workshops, have programs, write a book, get a podcast, all the things (which happen over years and years of time, especially if you're doing it yourself), she became so much clearer about the steps she needed to put in place in her plan. She could ignore everyone else's version of success and start creating the life and the business that she wanted, not the one she thought she needed to have.

What Happens When Success Doesn't Feel the Way We Thought It Would

This is actually one of the big ideas behind my one-woman show, Chasing. What happens when success doesn't feel like the way we thought it would?

I worked with a client who, along with two friends, sold a business for 75 million dollars. His cut was 25 million, but he found he wasn't happy.

So what happens when we keep believing that the next achievement will finally make us feel satisfied?

Goals aren't the problem. Goals are amazing. Goals help pull us forward, help us reach our dreams. Achievement isn't the problem either. The problem is that we keep chasing more. We want to do more, be more, have more. Maybe we feel that pressure from society outside of us. Maybe we feel that pressure from inside by the saboteurs pushing us forward. But we don't stop long enough to ask: Is this the life I actually want to live?

I can remember a client saying, "The next step for me is to get a promotion at work.” 

When I asked her, “What do you want?”  She said, “I actually want to quit my job, be a stay-at-home mom, and do crafts and make grilled cheese sandwiches."

I said, "Then do that." 

"Yeah, but it's not like a BHAG — a big, hairy, audacious goal.”

"It doesn't have to be. Would that make you happy?"

She said, "Yes, it totally would."

"Great. Then that's what you do."

Do what will make you happy (within reason). You have to pay your bills, take care of your kids, all that stuff. But if your life is allowing you to make that choice, do it. It doesn't have to be the biggest, most impressive goal to count.

Why High-Achieving Women Need Space More Than They Need Another Goal

Women need to have that space to step out of the day-to-day and really look honestly at where they are: a bird's-eye view. Then the coaching to help them see what they may not be able to see on their own. Some things are right in front of us, and we have our blinders on, or we're just not noticing them.

Then having other women around them who understand ambition, who understand, "I want to be successful", but also understand the pressure that comes with it. Because as you move into the next level of success (six figures, multiple six figures, seven figures), you probably now have a team, more staff, more expenses. Maybe you buy that bigger house, and now you have the pressure of more expenses. The pressure can come with success, not just before it.

The goal isn't simply to accomplish more. It's to create success that also feels satisfying.

Maybe You Aren't Behind After All

Maybe you've simply become so focused on what's next, the next goal, the next achievement, the next thing in line for your success, that you've just stopped noticing how far you've come.

So many times we get to the top of the mountain, and we don't look back. We don't see how far we've climbed. We have to do that.

Maybe your next step isn't another goal. It's just making a plan that goes with the goal, and finding the accountability and support to actually follow through. Having that space and support to decide what you genuinely want next.

Success and feeling like enough, success and satisfaction, rarely arrive together automatically. The gap is worth looking at, not outrunning it, and not feeling the pressure to do even more.

If you want that space, that coaching, and that community of women who understand both the ambition and the pressure, I'd love to have you in my She's Goaled Group Coaching Mastermind Program. 

Doors are open now and close September 4th at 11:59 PM Pacific. It's application-based because I keep the groups small to make sure there's the right mix of people and the right fit for you. 

If you have any questions, feel free to email me: [email protected]. 

Listen to the full Dynamic Women podcast episode here.​

Or watch the full YouTube Video here. 

Until next time, stay dynamic!

Diane

Frequently Asked Questions

Why do high-achieving women always feel behind despite accomplishing a lot?
High-achieving women often feel behind because they move the finish line immediately after reaching a goal, leaving no time to acknowledge or celebrate what they've built. The focus shifts instantly to what's next, what's missing, or who else is further ahead, creating a constant feeling of being behind even when objectively succeeding.

Why doesn't success feel satisfying for high achievers?
Success often doesn't feel satisfying for high achievers because the goal was never clearly connected to what they personally wanted, only to what they thought they were supposed to want. When success is measured by external achievement rather than internal satisfaction, reaching the goal rarely delivers the feeling they were expecting.

How do I stop comparing myself to others' success and timeline?
The most effective way to stop comparing yourself to others is to get clear on what success looks like for you specifically in this season of your life, not someone else's season. Everyone is running at a different pace, with different resources, responsibilities, and starting points. Comparing your chapter one to someone else's chapter ten is never an accurate measure.

What should high-achieving women do when they feel behind?
Rather than pushing harder, high-achieving women who feel behind often benefit most from stepping back to see what they've already built, getting honest about whether their goals actually align with what they want, and finding support and accountability from women who understand both the ambition and the pressure that comes with it.

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I'm Diane Rolston, award-winning life and business coach, professional speaker, podcast host, and founder of Dynamic Women®. I help high-achieving women create success that actually feels satisfying, not just impressive on paper. Learn more at dianerolston.com.