Life Lessons through Entrepreneurship

I’m building an app.  

There.  I said it.  

I’m building an app and I am not ashamed that there’s a possibility I may publicly fail.  (Lie #1)  

From here on out, I will shout from the mountain tops to anyone who will listen that I, Ashley Williams, have committed to the potential of something great.  I refuse to shy away and cower in protection of this small, nearly nonexistent thing I have poured so much of my time and energy into.  I have great confidence that this work of today will be the shinning foundation of the future I am creating for my tomorrow.   (Lies #2 and #3)

I have not been on this entrepreneurial journey for long, but I’ve certainly learned a lot along the way.  These are some of the lessons that building an app with no skills in development have taught me.

Lesson #1: Entrepreneurs lie.  A lot.

Before you throw me off the deep end, let me explain.  I am not the most confident person you’ll meet on the street.  Yes, I successfully completed high school, went on to earn a degree at a university 2,000 plus miles from home, jumped into an MBA graduate program having absolutely NO background in business and decided kick the 9-5 for the freedom of the entrepreneurial life.

Who exactly knighted me with the authority to do that?  No clue, because I am one of the greatest instruction followers I know.  (I mean, not all the time, but let’s say relatively speaking.)  Give me some directions and I’ll get to the final product.  Tell me what to do and I got you.  Break down the gist of what you’re generally looking for and I will run like the wind, returning with a result that will likely surpass your initial expectations.

I am great at taking orders.  I never really like the restriction, though — so I’m the queen of taking someone else’s structured something and making it my own.  (Yeah, I’m that chick in your Sip and Paint class that asks for colors that weren’t offered on the palate and ends up with the same background in her painting as everyone else but a completely different focal point.)

Now, all entrepreneurs may not necessarily lie to themselves as much as I do, but I know confidence is a major part of most entrepreneur’s success.  We all know someone (maybe it’s you) who always has these awesome ideas but is too afraid and comfortable to leave the front porch.  

In essence that was me, but I no longer wanted it to be.  So I lie to myself.  Daily.  I try to work like I already have the wildly successful business.  I talk to people as if my app already exists and I sell it as if I can’t believe you aren’t already using it…when in reality I have nothing.  I’ve learned that if I don’t believe in the possibility of it, why should anyone else?

In the wise words of my father, “fake it til you make it!”.

Lesson #2: The magic is in the execution, not in the details

I’ve hit this entrepreneurial lesson hard. Multiple times. And honestly, this lesson really teams up with the mantra of “there is nothing new under the sun”.

I don’t think it was necessarily silly for me to believe that there is “nothing else in the market available like this” or that my idea would be the prototype for “x” industry, but the reality is, people will use the resources they have to find the solutions they need with or without your business — and many times there’s already a system in place to do so regardless of how inefficient it is or not.

So…then the magic is in the details, right?  


At least not for me.  Even now I’m still working to remind myself that the magic is not in what I’m offering, but it’s execution and efficiency.  In the beginning, this was really hard for me to understand.  I’m an analytical girl who’s always dissecting her detailed world but the ever growing tasks and due dates on my to do list are constant reminders to let that go.  

I just don’t have time to focus solely on details if I want to execute!  Every day I’m reminded that striving for perfection only leads to unmet goals.

Lesson #3: Understanding your personality, work style and motivators is more than half the battle to success.

Man oh man.  This is something that’s become very apparent in many areas of my life, from relationships to fitness.  Entrepreneurship has proven to be no different.  

Until I got to the point where I realized these were important factors of my productivity, I was fake productive.  No, really.  I’m good at spinning my wheels without necessarily reaching any goals.  Throwing things together that aren’t quite cohesive enough to create value was a never ending thing.  

The A for effort felt good though…until it didn’t.  Eventually I had to come to terms with who Ashley is.  Once I was able to truly see myself in the mirror, it hit me:

  1. I cannot function successfully without structure — even if that means it will cost money.  From killing it in the gym with crossfit to joining the Apps Without Code Bootcamp, I do much better when I have a set plan to follow, an accountability group to check in with and a to do list to cross reference.
  2. I need the freedom to explore who I am in my work.  Anything that’s too restrictive is depressing and frustrating.  I’ve got to be able to express who I am and explore what that  means in an environment if I’m going to be successful.  So yes, I need to change background colors, fonts and screen layouts.  It’s imperative for my sanity!
  3. Sometimes I just need to strive for good enough.  That feels horrible to say aloud, but I finally understand that my over analytical virgo mind will get the best of me and my productivity in the small details if I allow it.  Every day I have to consciously make a choice not to get wrapped up in details that will hinder my progress and execution.  Some stuff can wait to be picked over later.  When it’s time to focus on the bones, commit to focusing on the bones, Ashley!
  4. Bite sized goals help me keep a healthy appetite for success.  Like anyone else, I get tired.  I may start out excited, but sometimes I just lose steam.  Call it elementary, but small, attainable goals are very important to me.  It’s a lot less likely that I quit if I make progress palatable and give myself plenty reasons to celebrate.  So yes, I’ll take my “Awesome Work!” star sticker, please and thank you!

I’m forever grateful for these entrepreneurial lessons but the crazier thing to me is how translatable they have been in my life as a whole.  Overall, I am confidence building daily and know if I keep putting one foot in front of the other, I’m bound to accomplish all those deferred dreams in due time.

Watch me work!

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Create space and declutter to make dreams a reality!

cluttered books and computer workspace

I’m not a hoarder, per se…but…I’m a hoarder.  

The funny things is I try to blame it on the nature of my business.  I work with kids.  Kids need a lot of stuff (in general).  We do a TON of crafts.  Kid craft materials usually look like trash (let’s be real: sometimes the final product look like trash, too LOL. But I digress).

If I’m being honest, though, the empty egg cartons, paint jars and pipe cleaners we use for our vertebrae projects are not the only things that define me as such.  

I have trouble throwing things away.  

Magazines I’m going to read “when I have time”.  Textbooks from college that I NEVER look at but feel are just “good to have”.  Clothes I’m “working hard to get back into” or T-shirts I’ve collected over the years.  So.  Many.  T-shirts.  I mean, you should see my Gmail inbox.  It’s ridiculous!  And we won’t even get started on the coupons I hoard only to forget about since I’m usually headed to the grocery store in a scramble anyway.

Every now and then I think about becoming a minimalist.  Life should be simpler.  I know it can be, and I want it to be!  I really do!  But every time I start to get rid of things I get sentimental about the middle school graduation t-shirt we received AGES ago with all my classmates names on them.  (Many of which I didn’t know to start…)  Or my coins.  Thinking about the money I could save if I do buy is the reason why I hang on to those stupid coupons when I KNOW it’s not likely that I’ll spend that money on those products or services anyway.  

I’m a mess.

Decluttering is something I’ve always known I need to do with stuff, but it wasn’t until I started tap dancing around the idea of being an entrepreneur that I realized the importance of doing it in so many other areas of life.

Let me explain.

I’ve always been fairly careful and calculated:  Carefully follow the road map to get to the destination.  Calculate the risk of desired deviations.  Enjoy the fruit of your decisions.  

What that usually meant, however, was I ALWAYS committed to the safer option and was only okay with taking risks that would allow me just enough slack on my experimental rope to safely come back to the original plan unscathed.

I liked it this way.  It allowed me room to play with the idea of controlling my own destiny, but the security of knowing I couldn’t jack my situation up too much.  I needed my safety net.

But you know what?  It didn’t take too long before the pattern of hitting my head against the same brick wall of misery became a more consistent, recurring thing.  

I began to realize that holding on to security was making me emotionally sick.  Being safe just left me sorry.  The concept of being an entrepreneur and working for myself, envisioning a lifestyle and actually chasing after it became more and more appetizing.  

So I sat on idea after idea, year after year, working my 9-5 job, waiting for the “thing” that would allow me to safely transition from a life I despised to the life of my dreams.  And after years of trying to make it happen but only being able to experience a morsel here and there of the life I truly desired, it hit me:

Entrepreneurship is not safe.

That was a tough pill to swallow.  It was SO against my personality.  It was the total opposite of what I felt made me the responsible adult I was always striving to be.  It was scary.

But eventually I came to a crossroad: you can either continue down this safe path to entrepreneurship, only to experience a fraction of what you’re hoping to create for yourself down a long road, OR you can buck up, muster up every ounce of courage you can manage at the moment and create space in your life to allow those dreams of yours to become your reality.

It gave me a headache.

I fought to get around it.  I tried to make my dreams the best side hustles I could possibly manage.  I worked damn near ‘round the clock.  I tried to give every moving piece of my life the time it needed and deserved to be what I longed for it to be.  But the reality is, in all my efforts, the main thing I accomplished was learning a plant can only grow as big as the pot it’s placed in.

My dreams had reached capacity.  My life could not receive anything greater than it had room to.  I had to declutter not ONLY my life of physical “things”, but of my obligations, responsibilities AND commitments if I wanted to receive the fullness of what I felt I was working towards.

Choosing to declutter was hard.

It meant I had to ditch the safety of the job I had.  I mean, I hated it, so emotionally detaching from the physical location was easy.  Emotionally detaching from the consistency of that check?  Was not.  

Now, I won’t pretend like I was that corporate business woman who was working a 300k salary job, stacking chips and enjoyed end of the year bonuses that matched some other’s annual salary.  Nah, that wasn’t me.  But all my bills were paid and new stamps in my passport were something I could prepare for.  So, knowing that decluttering meant I needed to leave the job that allowed me to be a financially independent adult was not a strong desire.

I panicked.  

I quit my job, but only to fill the void with other long term temporary gigs that were not consistent with my dream to soothe my fears.  And you guessed it.  I was miserable there too.  But you know what?  That’s okay, because the transition was good for me.  It was necessary for my personality because just as it’s tough for a drug addict to go cold turkey, I needed to take baby steps to prove to myself that what I was doing was the right decision for me; to give myself permission that I could if I wanted.

So I opened my mind and schedule up to the possibility of receiving the life I dreamed of.

This part of my life was tricky.  

I was in a serious limbo dance between the known and unknown.  On one hand, I had a contract with a defined end date that I was glad took care of the expenses of the “right now”.  But looking out into the future?  I couldn’t tell you what was to come.  All I knew was I had a skill set that I hoped and prayed would carry me through to the successful side of entrepreneurship.

So I focused on just putting one foot in front of the other.

This worked, but eventually the moment came where I reached yet ANOTHER fork in the road: either continue pouring all your time into working for someone else’s goals and mask it as “successful contract work” or get serious about you and put yourself first.  I knew that if I continued down this route, I would only hinder the transition towards my personal work and aspirations becoming a priority.  I knew I had to jump with no net.  I had to cut back.

I remember the day I communicated this to my client.  All I could think to myself was “you’ve got some nerve, Ashley.  Who do you really think you are?!”  I can say, I’ve never had a moment quite like that where I truly had to think about my response to something I asked myself.

I had reached a moment where I needed to answer my own question.

So I made some defining decisions: I AM an entrepreneur.  I am in control of my career and financial destiny.  I am choosing to DO something about that which I long for and I am going to prove to MYSELF that I can.

And I kid you not, just like that, as if a divine intervention was just waiting for ME, the moment I decided to make myself available to the lifestyle I wanted was the minute I found I was able to receive the work that matched that dream.

Duh…so simple, but so not simple.

I had to finally acknowledge that I could not carry the bigger package if my arms were full of the small trinkets.  I had to be okay with putting those down to make room for the greater goal, and my goodness, has it been worth it.

Now, I am not the one to sell a dream.  Letting go of something of great value in hopes of gaining something that could potentially have more value felt a little crazy, and so far the ride has certainly not been all unicorns and rainbows.  There have been plenty of hurdles and clouds.  It can be an emotional rollercoaster.

I remember my first summer out of the 9-5 structure.  A seasoned entrepreneur would probably just call it being in between contracts.  The paranoid me called it unemployed.  Every day was a constant fight to remember I was experiencing the ebbs and flows of business and this “unemployed” status I was experiencing was only temporary.

But I am grateful to know that the life I choose to live today is creating the life I am working so hard to enjoy in full tomorrow.  

Each day certainly gets a little easier to create space for the life I yearn for.  So far I can say it’s totally worth it.  I’m very grateful to have arrived to the belief that a life of living boldly holds much more value than living a life in “career fear”.

I’m so thankful for the courage to pursue those dreams deferred, today.

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