Photo by Daria Nepriakhina on Unsplash

“Forgive yourself for working in someone else’s dream, while searching for your own.”

Several weeks ago, I found myself in a virtual room filled with several budding entrepreneurs. It was a frantic, hopeful energy that is only understood, and appreciated, within the breed. We got lost in world-changing vision & big ideas. It was intoxicating.

The ladies then dispersed. I watched each carry that passion into the next conversations & hours online. Then slowly, the magic evaporated and I was left with overwhelming guilt.

I had gotten so wrapped up in the group’s energy that I neglected to share how brutal my own three year entrepreneurial journey had been.

The next morning I felt compelled to share “6 Real Truths You May Not Know About My Journey”.

  1. REVENUE:  I had to get a part-time job for six months last year to fund this dream.
  2. SALES: I didn’t land my first corporate client until well into Year #2.
  3. FEAR:  Every morning for the first year, I looked & applied to job postings.  No one would even see me for an interview.
  4. SACRIFICE: My husband has always been supportive of me but we have both sacrificed a lot for my dream. I carry guilt for that.
  5. RELATIONSHIPS:  I have lost countless friendships since starting my business.  I stopped making them a priority.  There’s guilt there, too.
  6. INDEPENDENCE:  I’m grateful for my husband’s income.  But I lost a part of my identity when I was no longer an equal contributor.

The email got more replies than any I’d ever sent before. One of them came from a young entrepreneur in her first year of business.

She responded:

“Thank you so much for your words & honesty. I resonate with all of them – the guilt, the applying for jobs when I’m having a bad week, etc. Your realness continues to be a guiding light for me, so thank you. How can I help [your business] or you this month?”

I asked her to pay it forward by sharing her own lessons from the first year in business.

That work follows for those who need it.

Lessons on Entrepreneurship From My First Year Living It

Photo by Thought Catalog on Unsplash

If you told me just a year ago that I’d be where I am today, I would have laughed. Hard. 

Leaving my corporate, cushy job for the great unknown of entrepreneurship? Impossible. 

Layer a pandemic on top of that, and well, you’ve got a fantastic story in the works. 

Yet somehow in October of 2019, I said goodbye to my mid-level management role with a company that let me travel and launch marketing campaigns with little-to-no-supervision and jumped head-first into a lot of little projects that somehow morphed into a career of freelance work. 

It has been quite the journey – one I never could have predicted or prepared myself for. 

Here are the top three things I’ve learned over the past nine months: 

Just like any passionate relationship, there will be extraordinary highs and lows to encounter. 

Today is a good day, but to be honest, a good day is a precarious thing for an entrepreneur. 

The days when I have great collaborative calls, receive positive feedback, and feel as though my business is moving in the right direction, I feel unstoppable. These are the days that keep me hooked on the dream. 

And then there are bad days. And these bad days feel as though they will stretch on forever and take away any chance I had of success. For anyone like myself who struggles with anxiety and depression, these days can be unbearably potent. 

But despite the highs and lows that have come, I’ve discovered that the only way I will survive is by creating routines and systems that validate my feelings and support my vision when I’m not strong enough to do it alone. 

On days when I feel a bout of depression or anxiety settling in, I ask myself to pinpoint the negative source. Once I’ve identified it, it somehow has less of a hold on me. On the bad days, I let myself bow out of any obligations that aren’t essential. I practice self-care. And I remind myself that this feeling won’t last forever. 

And on the good days, I push myself to go harder, dream bigger, and move faster. It’s a delicate balance, but the most important thing to remind yourself is that if this were easy, everyone would do it. And for that alone, you should be immensely proud of yourself. 

Saying “yes” will teach you far more than a course or book could. 

Sure, I’ve wasted some of my time by sitting on calls that ended up being fruitless. And yes, I’ve taken on projects that have made me question my ability to do the work. But each of these experiences allowed me an opportunity to learn something new about myself. 

Whether it has pushed me to niche down my services so I stop failing at things I’m just not good at, or has helped me to practice bowing out of opportunities where I’ve seen one too many red flags with a potential client, every yes has shown me something I never would have learned otherwise. 

Many of my favorite projects and clients to this day came from my saying yes to an initial conversation where I wasn’t entirely sure it was going to work out. 

Say yes, even to things that don’t immediately make sense or seem scary. 

Setting boundaries is essential in order to sustain an entrepreneurial career. 

It took me quite a few months into my journey as a small business owner to understand what was missing and consequently causing my anxiety levels to skyrocket at all hours of the day and night. 

Boundaries come in multiple shapes and sizes, so it’s important to identify which ones you need in your own life. I finally started pinpointing where my breaking points kept occurring, and then set up boundaries to prevent that from happening. 

For example, if I have a particularly busy day, I find a few fifteen-minute segments where I can sit in the sunshine to recharge. Or if I have a project or client who is destroying my mental health, I find a way to move away from the situation for my own sanity. 

In recent weeks, I’ve discovered the key to taking a full day (or days) offline: plan the date, tell your clients a week in advance, and then repeat that sentiment that entire week leading up to your days offline. 

Setting boundaries with yourself is the most important part. 

The entrepreneurial journey is not for the weak of heart. 

Never in my life have I been more unsure of my ability to be successful. 

And yet, I keep coming back, opening my laptop every morning and diving into the world of possibilities. Because when you work for yourself, the opportunities are endless. 

Your ability to learn, grow, pivot, fail, and succeed keep you moving, entirely too curious to see what the next chapter’s cliffhanger will be. 

For those just starting out, understand this: some days this will simultaneously feel like the best and worst decision you’ve ever made. 

And in those moments, remember – you’re not alone in any of this.

“Vulnerable work inspires more of the same.”

Huge thanks to Samantha Rosenfeld— freelance writer, digital marketer, journalist, and fearless entrepreneur. May her vulnerability inspire more of the same.


  • Stacy Cassio

    Founder / CEO

    Pink Mentor Network

    Stacy Cassio is the Founder & CEO of the Pink Mentor Network. Stacy understands the importance of mentorship because her own career & business have been built on the opportunities introduced to her by mentors. In 2017, Stacy Cassio founded the Pink Mentor Network, Charlotte’s 1st female mentorship community.  Followed by the creation of Pop-Up Mentor, a brand new way to mentor in 2018.  Stacy is dedicating her life to reshaping how individuals seek & obtain mentorship, and helping organizations build cultures of mentorship.  In 2019, her work was nominated for the Athena International Corporate Award for Leadership and Charlotte Inno’s “Opportunity Champion” award.  Stacy also was named a Mecklenburg Times 2019 Phenom.  Stacy’s career was built & fueled by great mentors until she became one.  IG:  @pinkmentornetwork FB: @popupmentor LI:  @stacycassio