Foolish Beginnings, Messy Middles, and Mastery

What does it really take to build something from the ground up—and keep going when it gets messy?

In this solo episode of Unapologetically Yours, Ashley Logan reflects on what it means to start something new, navigate the uncertain middle, and arrive at a place of grounded mastery.

She shares her own entrepreneurial story of founding her marketing agency “Yakkety Yak” in 2012, scaling it through many iterations, and learning how to lead from a place of authenticity and alignment. And now, as she starts a brand new business working in somatic healing, coaching and workshops, she’s embracing her own beginner’s mindset all over again.

This is an episode for anyone at any stage of the journey—whether you’re dreaming of starting something new, knee-deep in the messy middle, or refining what already exists.

 

In this episode, you’ll hear about:

✨ Lessons from 12+ years of entrepreneurship 

✨ The difference between foolish beginnings, messy middles, and mastery

✨ Why it’s okay (and necessary) to stumble when you start

✨ How to stop comparing your journey to someone else’s

✨ Why boundaries, rest, and team support matter more than ever

✨ The beauty of not knowing exactly where it’s all going—and doing it anyway

 

Whether you’re launching a business, stepping into a new season, or redefining what success means to you—this episode is a powerful reminder to trust your inner compass and follow the call!

 

Connect with Ashley:

Instagram @ashleydlogan

Website https://ashleydlogan.com/

 

Have a topic or guest you’d love to see featured on the Unapologetically Yours podcast? Send us an email: [e-mail] 

 

Keywords

entrepreneurship, beginnings, mastery, business, personal growth, storytelling, self-discovery, resilience, creativity, purpose

Episode Transcript

(00:00):
When you're thinking about starting something new, oftentimes you're comparing yourself tosomeone who maybe is in the messy middle or is in a state of mastery, and that's not fair
to yourself.
Hello and welcome to the latest episode of the Unapologetically Yours podcast.

(00:21):
I'm your host Ashley Logan and I am so happy to have you here today.
Unapologetically Yours is a podcast where we go deep on everything from spirituality torelationships and connection to business and belief system because in a world when we've
been taught to play by the rules, it's time to live unapologetically and that's exactlywhat we're doing.

(00:41):
And so today we're gonna talk a little bit about beginnings.
messy middles and mastery.
So I want to give you a little bit of background on moi.
I am a long time entrepreneur.
I founded a content marketing agency that's based in Chicago called Yakity Yak in 2012 and2014.

(01:05):
I hired my first employee and I have been chucking along ever since.
And you could say that I am in the mastery stage of
Being an entrepreneur and I don't even know what mastery means.
think mastery means being open to the possibility of being wrong I think mastery meansbeing open to the possibility of doing things different and I think mastery means having

(01:30):
the confidence to hand things off Take things off of your plate and hand them to otherpeople who are smarter and more effective and all of those things and Having the
spaciousness to do that and that's really sort of where I'm at in that
journey.
Yaketyak has gone through a hundred different iterations since I started it.
And where we landed and what our true North Star is that we want to make a difference inthe world by serving purpose-driven brands and businesses and helping other entrepreneurs

(02:01):
to use their voice in a way that can make an impact, reach the right people and tellstories that resonate.
I started Yaketyak because I wanted freedom.
I had spent the last five years working in commercial real estate at 100 % commission andit was a totally, totally wild west type of environment where you eat what you kill and

(02:29):
there's a lot of competition around it and I loved it.
I thrived.
I thought that it was, though it was cutthroat and there was a lot of things that I wouldhave changed about the industry overall.
I learned so much about what it means to be an entrepreneur and that prepared me for thehighs and the lows.
And let me tell you, there are so many highs and lows about running your own business.

(02:52):
And I, my cute self thought that starting a business meant that I was going to have fullcontrol over my schedule and that I was going to make tons of money and that I was going
to, you know, build and scale and grow and maybe sell and all of these things.
And
Some of those things turned out to be true.
And then a lot of those things were not because ultimately when you are an entrepreneur,there's no one else that you share the load with unless you are smart enough to start a

(03:21):
business with a partner, which I was not.
It was me solo and wearing all the hats as needed and taking them off when possible andjust sort of building this company.
on a grassroots basis with no outside investors, no institutional funding and doing it allmyself.

(03:42):
And that felt good for a while until it didn't.
Doing that while having three young kids and at one point we had over 30 employees.
We're doing, I think, around 4 million in revenue.
And it was really exhausting and hard.
But I would do it all again in a nanosecond because there is something so

(04:04):
gratifying about having a vision and planting the seeds and then seeing it come to life.
And that lights me up in so many ways.
And also working closely with clients who are trying to make the world a better place andfinding a solution for them to tell their stories and make an impact in the world.

(04:24):
It's like, chef's kiss, just the best feeling ever.
Like I said, if we're looking at things in terms of like, hmm.
being in the beginning stages of things, which can be a lot of fumbles and then in themessy middle.
I would say that Yakty Yak over the years has just really oscillated from as we continueto refine and redefine and grow and change and as new people come through the doors and my

(04:54):
vision shifts and changes, we've been able to embrace change.
and try to adapt to what's happening in the conditions in the marketplace and try to serveour clients with integrity.
And it's been a lot.
There's so many pros to running your own company from having that ability to make thosebig decisions to not having someone who's going to have to tell you what to do.

(05:17):
But part of that means you have to be prepared to tell other people what to do and holdthem accountable and hold your vision at the highest esteem so that you can be the North
Star for the people who are working with you and on your behalf.
who hire you and all of those pieces.
And so it's a lot.
But I want to say this.
If you are thinking about starting a business, do it.

(05:40):
Do it.
It is awesome.
So I shared something on my Instagram fairly recently about foolish beginnings.
And gosh, I'm so good at foolish beginnings.
I have reinvented myself.
I start new things all the time.
I'm so wildly curious.
I can't get enough of new.

(06:01):
But when you're thinking about starting something new, oftentimes you're comparingyourself to someone who maybe is in the messy middle or is in a state of mastery.
And that's not fair to yourself.
There is something so beautiful about just starting and taking the steps and planting theseeds and doing the thing and being unapologetic about how that looks to the outside

(06:26):
world.
because you are allowed to stumble in the beginning.
You are allowed to learn as you go.
You are allowed to change the game as you learn the rules.
And all of that is part of starting and that's all part of the journey.
And yeah, it takes courage.
Also, it's fun when you let it be and you stop looking at what everyone else is doing andfocus only on you, the North Star.

(06:53):
know that every day that you are making progress, you are making progress.
And if you are comparing yourself to someone's middle or someone's end, then you're nevergoing to feel like you're good enough.
So focus on the things that you did do.
Focus on the things that you can do and the things that are within your control andcelebrate those victories because it makes all the difference.

(07:15):
So I can talk about this with some level of expertise because a year ago I started apodcast and I
I had never done a podcast before.
had helped produce many other podcasts, but I hadn't been the host.
And so I allowed myself to stumble and make mistakes.
And I am sure that there were plenty of people who are like, the fuck is she doing?

(07:40):
Who does she think she is?
And don't worry about that.
Don't worry about what anyone thinks because as you continue to grow and align in yourmission and align and get your voice and get your bearings,
people see that and it resonates with them and then they celebrate it for you.
The people who you are meant to resonate with will see you and you will have thatresonance.

(08:04):
so being in the messy middle is a fun and beautiful thing sometimes.
I also have started a new business where I help support people in accessing their passion,power and purpose through somatic
practices, creative workshops, and retreats.

(08:25):
And I am in the foolish beginning here.
I have had so much fun learning these skills and introducing them to new audiences, butI'm not exactly sure where it's going to go.
I'm not exactly sure who I'm going to show up in service for or how these events or howthese workshops or how these retreats are going to unfold and who's going to show up.

(08:47):
And there is so much beauty in the unknown because
being unattached to outcomes or comparing myself to other people has allowed me to welcomein whatever will be.
And that could mean invitations to lead new experiences.
Like for example, I was invited by a peer to lead a segment at a retreat for little girls.

(09:12):
And basically it was a day long workshop where girls learned everything from self-defenseto
art and I was able to lead mindfulness and breath work for these girls and teach them howto breathe, to get presence, how to not lose their tempers, and how to fall asleep through
different breathing patterns.

(09:33):
And that was so cool and that never would have happened had I not just begun.
If you're looking or interested or have an idea on your heart or in your mind, keep going.
Plant the seed.
Allow yourself to
Be a foolish beginner.
Allow yourself to stumble through day one.
Allow yourself to learn from your own mistakes and allow yourself to be present on thepath of creation because it's a beautiful and wonderful path.

(10:02):
And when you get to the messy middle, you get to look back at the path and how you gotthere and reevaluate and decide what do you want to take with you?
What do you want to leave behind?
And create the foundation for the next step when you get to enter that.
mastery phase.
the most important thing about being in mastery is to keep learning, keep evaluating, andkeep aligning that North Star back to you so that you can stay on course and create the

(10:31):
life of your dreams.
Entrepreneurship is, as my dad likes to say, it is not for the faint of heart.
And shit, man, it ain't.
But I know a few tools.
for how to strengthen your heart so that it does fit for you.
And part of that is by not comparing yourself to those around you.

(10:54):
Don't compare your beginning to someone else's end or middle.
And also hold tight to your vision.
Keep asking yourself, is this what I want?
Does this work for me?
Is this aligned?
So that you can stay in flow and create a business that serves.
Your greatest good, your highest good, and your highest self, and the people around youwill want to be part of that as well.

(11:18):
And the next piece that I think is so important for entrepreneurship is settingboundaries.
Know what works for you and know what doesn't, and hold tight to that so that your timedoesn't get away from you.
It's so easy to think that you are responsible for every single choice and every singledecision, every single blah, blah, blah, blah,

(11:39):
You do have to hold tight to some of those things, but not all of them.
So at the earliest opportunity, start to let go of the things that you're squeezing sothat you can build a life that has ease, that's not working harder, but working smarter.
We've heard that phrase before, but it really is true.
It is so easy to get to a state of burnout when you're running your own.

(12:01):
show, whether that is being an entrepreneur of a major marketing agency or trying tocreate something in the storytelling realm or trying to start a somatic healing something
or other.
Life is beautiful.
It's messy.
Your big ideas matter and the impact that you can make in the world is significant.
So go out there, do the thing and know that when you are following your heart, when youare following your inner compass, that won't lead you astray.

(12:31):
Thank you so much for tuning in today.
I hope you have a beautiful day.
Go out, do the thing, make some mischief in the world because mischief is where it's atand everyone needs a little smile and a little fun.
Remember to follow, like, share, comment, send us a note, do the thing because we want tohear from you.

(12:52):
And until next time, I'm Ashley Logan and I am unapologetically yours.