This Audacious Entrepreneurial Journey: Lessons Learned from Two Years in Business

In the past week, I’ve…

  • Met with 5 different clients, 2 prospects, our accountant, 2 team members,

    a design partner, my CEO peer advisory group, and my business coach.

  • Reviewed the final round of revisions for a client’s new website

  • Prepared another client for a meeting with their Board of Trustees

  • Planned webinar content with a client and their customer

  • Presented a strategic communications plan to a new client

I don’t share all of this to “glorify busy!”  I share it because, as I look back two years to when I was just starting Wythe Ave Consulting, my weeks looked very different!  And, I want to celebrate that transformation. In the beginning, my time was primarily spent finding the business – endless coffee meetings, networking, content creation – and running the business – legal, finance, accounting, development of processes and systems.  By design, my days were spent in Richmond, Virginia, rather than on a plane to Europe. But, I was wearing ALL the hats. It’s not that I wasn’t busy. The activities were just different.

reflection of plane

Today, I spend the majority of my time with clients or working to identify the team to support my grand vision: a firm with several fractional Chief Marketing Officers working with mid-sized businesses in driving distance of Richmond.

rollercoaster entrepreneurial journey

In celebration of my journey (which at times felt like a rollercoaster) and with acknowledgement that I don’t have all the answers, I would like to share a few lessons I’ve learned in case it helps others who feel like they’re starting something new – whether it’s a small business, a new product launch, or a wellness journey.

Begin with the End in Mind

What do you want to accomplish? How do you define success?  The goal doesn’t need to be so specific that you’re disappointed when things don’t turn out exactly as planned. But order of magnitude is important. And clarity of purpose is important.  Why are you pursuing this goal? How will you feel when it’s accomplished? What will be different about your day-to-day?

Look Within

Knowing yourself, your business, and your market, will enable you to position for success. As an exercise, take a few minutes to list all of your attributes or the features and benefits of your business offering. Now review the list and ask yourself,

  • Which make me (or my business) unique?

  • Which ones matter most?

  • Which feel most aligned?

When sharing your vision, focus on these things, rather than attempting to share everything.  

Ask for Guidance (and filter it)

If you’re embarking on a new journey, it’s impossible to know what lies ahead. But chances are, others have ventured ahead or have enough experience to ask questions that will help you prepare. I’ve found coaches and mentors to be invaluable during my start-up phase and beyond!  I suggest meeting with several before selecting one that’s the best fit.

Also, be aware of advice (solicited and unsolicited) that feels like it doesn’t align for you. With as much objectivity as possible, hear the opinions of others and independently determine your best path forward.


Express Gratitude

Throughout this journey, I have felt incredibly supported – by my family, by my community, by other entrepreneurs (even by those who may have been considered competitors!).  Particularly on days when it’s challenging, I take a few moments to capture my gratitude in a journal, write a thank you note, or let someone know the impact of their support. The process almost always provides an immediate lift, reminding me of my abundance, and helping others recognize the value of their contributions.   

Reflect on your progress

When I’m close to achieving a goal, my natural tendency is to move the bar or look to the next milestone – always trying to be better, do better, accomplish more.  Quite frankly, it’s exhausting, and sometimes counter-productive. I find when I force myself to reflect on what I’ve already achieved…on how far I’ve come…I feel a sense of joy and pride, which is far more motivating. Make a habit of journaling or writing articles that capture your thoughts and emotions, and periodically read your older entries.  Have a conversation with someone who is earlier in their journey. Look back in your calendar and note how the types of meetings or clients have changed. And, finally, celebrate your progress and accept your process!

Reevaluate your end game

Circumstances change. We learn along our journey. As this happens, ask yourself if the goal still makes sense. Don’t stubbornly pursue an end game that no longer serves you. Question whether it needs an overhaul or a tweak. And be honest with yourself about your reasons for the edit. Are fear and self-doubt trying to sabotage your success? Or do you truly need to pivot? If it’s the latter, repeat the cycle of looking within, asking for guidance, expressing gratitude, and reflecting on your progress.

I wish you well along your journey, and I’m happy to serve as a resource for you!