How I Got Through My First Year of Entrepreneurship

business owner entrepreneurship lessons learned Dec 26, 2021

How I Got Through My First Year of Entrepreneurship

I love what Fred Rogers says about self-discovery, “Discovering the truth about ourselves is a lifetimes work, but it’s worth the effort.” 


Starting my own business this year was a big lesson in self-discovery.  It was kind of like getting land in the Oklahoma Land Rush and being a participant on Shark Tank. 


While it’s the wild west of opportunity, there are many challenges coming out of corporate life that I experienced as I built my business in 2021. 


However, I would not give up the opportunity for anything. 


Regardless of the challenges, the effectiveness of the lessons I learned kept me enduring.


I launched the first-ever Gallup licensed daily planner called The Strengths Journal™ and I started my consulting company, Dana Williams Consulting, LLC.,  focused on leaders and entrepreneurs who wanted to live intentionally.  


While the lessons continue to come in each day, I am learning to accept the failure with the wins and know I am living my purpose.


I hope if you are considering starting your own business you will be able to leverage what I learned. 


Realize you cannot build your business alone.  

  • Establish a board of directors to help guide you. I selected a few gurus in my circle who specialize in finance, technology,  management, wellness, leadership, business consulting, and marketing. I was able to build my business with their help, and they did not charge me since they were my advisory board members from the beginning.  Though I didn't meet with each of them too often, I knew they were there for me whenever I needed them. 


  •  Join a mastermind group. I participated in several groups and in my experience, the groups with more experience were the ones I found most helpful.  I learned that I needed to get myself around people 3-5 years ahead of me to guide me as I had questions.  I love these folks in my mastermind groups and have grown from their wise counsel.  


  • Get a coach – find an experienced coach who will hold you accountable and be honest and transparent with you.  I had a lot of ideas and understood marketing, but my challenge was finding someone that would help show me the gaps and guide me as I wanted to move faster than some of my coaching groups.  Selecting a coach takes some time and you want to make sure they have the experience that you do not have and have produced good outcomes. 


  • Collaborate with like-minded entrepreneurs.  I never knew how much I would miss my office buddies and collaborators until I went on my own.  I knew right away that collaboration with other consultants would be very important and in teamwork their is strength. However, I had to be intentional to put in some time to find my people. There are some great folks in the consulting/entrepreneur space as well as some counterfeits.  I leaned on recommendations from highly respected people in my professional community to find the people that would help grow me. While this took some time, I got a lot of energy out of connecting with these folks and  they educated me from their expertise. We also helped each other support  our individual  businesses.  One of my favorite  African proverbs is "go fast, go alone, go together go further" and this became my beacon for finding collaboration partners.

Get clear on your unique talent and connect to yourself so you can serve others

  • It's hard to build your business from a purpose standpoint if you do not know what your unique talents are.  I was lucky that I had been working as a corporate leader and had the opportunity to unlock my unique talents through CliftonStrengths almost 10 years ago.  I am not naturally a disciplined person, so I had to make sure each day I was reminding myself to stay focused on my top 10 strengths and use them to build my business. I found a lot of value in finding other people to work alongside me that did not have the gifts I had. While some days I was more focused than others, I learned that is where my productivity and energy came from. If you are interested in unlocking your talents, you can go to to buy an access code and take your assessment. 


  • “No” is one of the best time management tips I learned.  As I built my mission, values, and goals based on my unique talents, I became really good at saying no. I had to get diligent about looking in my journal each week and reminding myself of my mission - which was to help people birth their purpose. I got so pumped when I was either facilitating a group or leading some 1:1 coaching sessions and saw the "light bulb" moment happen with my clients. It's one thing to know your purpose, but I had to keep a constant focus on what I was going to spend my time on and if it did not serve my purpose I had to say "no thank you." 


  • Keep tabs on your wellbeing –I learned from Gallup that 7 out of 10 people were suffering  with their well-being due to the pandemic and I needed to make sure I educated myself and kept a good handle on my health. I used the weekly score system in The Strengths Journal ™ and studied the new Gallup book Career Wellbeing to give myself a boost each week.  I found early in the year that my physical well-being had suffered during the transition from corporate leader to founder of my own business.  So, I started a new workout habit and changed my daily routine, returned to group training with my husband as well as scheduled a running date every Friday with a friend from 15 years ago.   

Look for frameworks and automate everything 

  • I learned that my growth hits a ceiling when things get complex.   So,  I built a business model based on my customer segments with a focus on value and customer service. I began to set an outcome for myself  and plan on accomplishing  3 things to finish each and every day. By planning this way, I learned to give myself permission that I did not need to complete a long “to do”  list each day that just keeps moving from day to day.  Instead, using my own framework of The Strengths Journal, I realized  I could get hyper-focused on what I could do with my strengths and get help if a task was not in my wheelhouse.


  • Technology is my friend (with a little help from others).   I became overwhelmed with the tech stack that I needed to run my business and realized I needed to overcome this mindset.  I solicited help from some amazing people that knew coding and online content management, however, it was not until I  allowed myself the space to learn, that I grew in this area.  It was a total mindset thing.  I can look back at this year and say I learned at least 10 new technology applications and because of that, I am saving time as my business is now automated.


  • Take time to reflect each day –“Test and Learn"  became my mantra as I began to build my business.  I shared this saying often with contractors who were helping me so together, we set a culture early on that  If we tried something and it did not work, we would not spend major time on it. If it did not bring an ROI, I changed the direction of what we were doing.  I learned to become comfortable with stepping out in fear and failing fast.   I love Donald Miller’s quote - Fear isn't only a guide to keep us safe; it's also a manipulative emotion that can trick us into living a boring life. 

Build relationships and bring value consistently 

  • Find your people- Everyone is not your customer. So, learning to focus on messaging to those that are my customer was very important.  Getting clear on my customer segments was huge and that comes from deeply understanding the problems my customers are facing.  My business is about solving pain points.  For me, that was working with corporate leaders and with entrepreneurs.  This took some time as I did get off track for a few months as I wanted to serve those that did not meet that profile but needed help. Once I had my segments identified, I was able to create vision boards and communications for them. As sales started coming in, I made a sticky note of the name of each new Customer and put on the wall in my “closet office” in front of me to look at each day. This way I kept my focus on them.


  • Creating Community – “Go Slow to go fast” was some of the best advice I got and applied it to building a community. I knew from my work at Southwest Airlines that the most important thing I could do this year is set up opportunities for community. So, I created two live monthly coaching groups on my website, joined Clubhouse, and created a weekly discussion space called Dominate Your Day Club for leaders and entrepreneurs who practiced using CliftonStrengths.  I also joined other moderators from other clubhouse groups to speak to my other focus topics on productivity and marketing. While we did not have a great number of sales this year from Clubhouse rooms, it became a place to build my brand and grow community.  I have met some of the most amazing folks on the app and had the opportunity to learn from each of them on a consistent basis.  I also was blessed to build relationships with other mods that spoke in my clubhouse and then take the content to LinkedIn Live, which we are now hosting twice a month.  I learned why it’s important to focus on who knows you, not who you know.



  • Value mindset -  As a new entrepreneur, I learned I could not communicate to my customers enough. So, I focused on bringing value to every meeting, every interaction, and each social post. That meant talking to customers on weekends when they needed something. Being available on a consistent basis and sharing resources each time we connected that would help the customers I was attracting. I learned to measure how I  knew when I have added value from Jack Malcolm who wrote Lean Communication and have this posted in my office:


  1. Did you improve the situation or outcome
  2. Did you improve the relationship
  3. Did you answer the questions asked?

I learned the best moments in life are not for sale.  They are in building relationships.  As we prepare for 2022, I feel like we are moving into a space of being focused on meaningful human interaction (not transaction)  and authenticity. I loved how Brene Brown mentioned in her new book Atlas of the Heart,  “If we want to find the way back to ourselves and to one another, we need language and the grounded confidence to both tell our stories and be stewards of the stories we hear.  This is the framework for meaningful connection.” I am thankful that we have an amazing tool to help people know their talents  in this unique time  as people are seeking meaningful work.  I could not be more excited to get into year two of my business and want to thank the many people that helped me live my mission each day including my husband, my daughter and son in law and my very energetic mother who is getting her degree in screenwriting at age 85.  The sky is the limit and we can't wait to help you get connected with your talents and design a live you love.


Happy New Year,



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