Published on:

1st Nov 2018

021: The Journey That Led Me Here (Dorothy’s Story)

If you’re looking for something a little different from Do Well & Do Good, you’ll want to check out its first mini-episode, where Dorothy dives deep into how she built a successful, flexible career for herself and where the advice she provides comes from. And going forward, you can now expect a mini-episode just like this one every Thursday!

In this minisode, Dorothy explains why she leapt from steady financial work to the startup sector, the struggles she endured launching her first business, and how those hardships influence her mission with Do Well & Do Good today.


Show Notes:

  • How did Dorothy’s parents influence her work ethic and career path?
    • Both were entrepreneurs much like she would become. She wanted to have her father’s flexible schedule.
    • However, being an entrepreneur wasn’t her focus when she went to college, instead aiming for job security and looking to work with a major accounting firm.
  • How did Dorothy enter the workforce?
    • She was hired on as an intern with PricewaterhouseCoopers and accepted a full-time offer at their Chicago office going into her senior year.
  • Why was she drawn toward entrepreneurial work?
    • She was introduced to a network marketing company, where she saw the opportunity to control her career without any limitations.
    • Realized her success was only governed by how hard she was willing to work.
    • Was introduced to personal development through figures such as Napoleon Hill, Eric Thomas and Les Brown, allowing her to realize just how much was possible to achieve in her life.
  • What Dorothy’s first startup experience?
    • Introduced to co-founder of an early stage startup in Chicago.
    • The business quickly became very successful and Dorothy received a crash course in business development.
    • Learned from her boss and mentor there that where you work is less important than who you work for.
  • Why did Dorothy leave the company?
    • That boss/mentor left, and Dorothy realized she didn’t want to give up her flexibility and autonomy.
    • Decided to strike out on her own.
  • How did her entrepreneurial career start off?
    • Was shaky the first few months as she didn’t have a plan. Made very little money and had to rent out apartment as Airbnb to make rent.
    • Really had to focus on her mindset at this time.
  • When did things truly change for Dorothy?
    • Her former mentor offered her a ticket to a workshop on Facebook ads.
    • Workshop host was offering a $30,000 coaching program. The price was steep, but Dorothy knew that she would have to give up if she didn’t pursue it.
    • Learned she had to take complete responsibility for her results and failures. Positivity and motivation were key.
  • Was this period difficult?
    • Yes; she experienced quite a bit of self-doubt.
  • What kept Dorothy pushing forward during this time?
    • Motivational books and podcasts were of great help.
    • Focused on giving and knowing that her generosity would come back around.
    • Also surrounded herself with a supportive network of successful people.
  • How did these struggles push Dorothy toward her current work?
    • She realized that she couldn’t wait for other people to help her, that to live the life she wanted and affect the change she hoped to see in this world she would need to take responsibility for it herself.


DM Dorothy on Instagram at @dorothyillson to let her know if you’ve made it this far. She wants to know who you are and thank you!

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About the Podcast

Do Well & Do Good
Create Success. Power Positivity.
This podcast tells the stories of people who have created financial freedom and leveraged it to increase their positive impact on the world.