The difficult side of being an entrepreneur

Being an entrepreneur comes with a steep learning curve and many obstacles to overcome. This list will help you to prepare for some of them. 

My daughter is a business student at Michigan State University. For one of her classes she had to interview an entrepreneur. You can imagine how thrilled I was that she chose to interview me. Given that I have been self-employed for 17 years and sometimes wonder if there is an easier way, I have decided to share my responses.

What personal doubts and practical fears did you have when you were starting your business and how did you get past them?


I left a salaried position with healthcare that offered a lot of security and perks. In the beginning without client success, it was hard to sell my capability. I didn’t have a track record to support the claims of what I was offering. I was afraid I didn’t know enough about the legal requirements to ensure that I was managing risk appropriately. When you have a boss, setting deadlines and being held accountable are part of the deal. When you are an entrepreneur, you set your own goals, milestones, and deadlines. It is up to you and you alone to hold yourself accountable. One of my early doubts was “ will I have enough discipline to follow through for myself?.”  I did a lot of writing and set an 18 month calendar. From that I was able to reverse engineer my priorities and goals. Follow through is something I am still working on!

How do you view and handle failure in your work?


Risk-taking requires pushing boundaries and anytime people learn something new there is clumsiness. The two biggest failures I have are the following:

  1. Taking a large client for granted: I had 80% of my business with one client and I didn’t continually listen to how their business model was changing. I had worked with this client for 6 years and felt very comfortable. They had made some new hires and I didn’t build enough relationship with the new team members. I think because of that my work did not seem as relevant and ultimately lost a renewal. It was a big hit and very painful. I am a much better listener now and value the entire ecosystem of the companies I work with.
  2. Not getting clear on the measurable outcomes of my work. I ran CEO roundtables for five years and did a lot of work on corporate culture and mindset. Recently I was asked to list the outcomes of my work and came up short. I didn’t pay as close attention to the management dashboards as I should have. Get clear on the value you offer, how your services are being used and how others measure your impact. You are going to need to prove your tangible and intangible value.

Worth a Read: The Female Entrepreneur – Women who run their world

How do you generate good ideas and effective solutions to solve complicated problems. Do you have a creative process you go through? 


  • I don’t think people understand the value of the internet for research. Early on in 2009 I spent a lot of time reading online, particularly @Twitter. I found that there were some people who were very insightful and good writers and I began following them and learned how to use software to extract insights. Clay Shirky’s wisdom is brilliant: the issue today is not information overload. I created a filter finding the smartest people in the world and created a way to listen to them. I also created a way to interact with them. The engagement process has given me so much joy and insight.


  • It is important no matter what industry you are in to get cross-pollinated ideas across industries so I recommend you go to at least one global conference a year. I am lucky enough to go to two a year. One is on the #futureofmoney called Sibos that will be held in Toronto this year. The other is on the dance between creativity and commerce held in Montreal called C2Montreal. I always meet fascinating people and get inspired by the energy and the intelligence in these places. These are not industry related events. Relationships and ideas outside my vertical allow me to serve in innovative and robust ways. Cross-pollination of ideas is what allows for platform-innovation, which is worth so much more space.


  • Be in a cross-functional roundtable in your local community. As sexy as it is to get ideas through leaders and global conferences, a lot of success is about being respected in one’s own local community. In Rochester, New York, there are 5 leadership roundtable options. In your community there may be more. Get engaged. Meet the diverse people in your community and learn from them. This is different than sitting on a civic board. It is sharing problems and brainstorming with others in your environment with an objective facilitator. You might not get an insight every meeting but in the course of a year, if you really invest yourself, you will get two or three ideas a year that can change the trajectory of your business. Peer-to-Peer learning is the roadmap for complex problem solving.

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What are some things you learned through being an entrepreneur that you wish you had known going in?

Retrospective: Discipline, discipline, discipline

Looking back I am sad it has taken me so long to keep good records. Until recently I did not keep good records on either the financial side or the client side of my business. I did only the paperwork that was required by State/Federal. This meant I did not write formal reports about business processes, client meetings, etc. Instead I always said, “I’ll get to that later”, even though I knew it was important. I just didn’t feel it was vital. Writing down plans, keeping excellent records, and tracking every penny are essential.

I am now much better at ensuring that I track my time, keep impeccable client notes, and write expense reports within 24 hours of a business trip. I don’t think people realize the level of discipline required to be successful as an entrepreneur.

Start-ups fail because people focus on the idea and not the business model. People underestimate how important building and maintaining relationships are. People think the only story they need to tell is to investors. Everyday is a day for executing a plan, appreciating and listening within your ecosystem and storytelling every step of the way.

Cheers to your resilience,


Do you struggle to find a senior, neutral woman to share your experiences with? Our mentoring programme is here to help you.

Jennifer Sertl Subscriber
Jennifer Sertl is an internationally respected author, keynote speaker & the president and founder of Agility3R. Agility3R is a training and development company dedicated to strengthen strategic and critical thinking skills.
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