Season 1,

90: Overcoming Illness in Business with Hilary Jastram

November 11, 2017

Hilary L. Jastram is the founder of J. Hill Marketing & Creative Services, an agency specializing in premier copywriting, editing and book editing for Fortune 500 brands and the “one-percent,” superstar entrepreneurs.

She’s an author, editor at The Good Men Project, and contributor to Influencive, The Huffington Post and The Mighty, among other large-scale publications.

She is also the founder of Sick Biz, “An organization dedicated to providing support, resources, hacks, and hope to entrepreneurs affected by chronic illness, pain, disability, and sickness.

Time Stamped Show Notes

[2:40] Hilary L. Jastram has started a nonprofit to support chronically ill entrepreneurs.

[6:00] Diseases are not about limitations, but adaptations. Day by day may look different but that’s ok.

[6:40] After some disfunction in her family and marrying and having children early, Hilary had no self confidence and was willing to take any job.

[8:25] Craving the validation while being in front of people, and after working at two news stations as a dispatcher, Hilary learned every news story was a tragedy and decided to focus elsewhere.

[10:22] She went back to advertising and marketing and found out she is really smart. That unlocked a part of her she didn’t know existed and she was determined to work at that capacity.

[11:28] One day, Hilary felt her feet swelling then tingling. And when drying herself after showering, she still felt wet.

[13:11] After 5 months of feeling worse each day, doctors were able to tell her she has chronic transverse myelitis and she’s being watched closely for MS.

[15:05] Working at a furniture store and sleeping 16 hours a day it was clear she couldn’t continue working, she didn’t have the stamina to even walk. devastating news, could be fatal, everything grinds to halt, vertigo 7 months furniture store, sleeping 16 hours a day.

[20:15] If depression was part of Hilary’s life it would be much more difficult though she used to have the victim mentality until she was tired of feeling out of control and decided to change it.

[22:50] Failing Forward Segment

  • Why did this failure experience happen to you? – “I needed to finally wake up and there was only one way to wake me up and that was the universe ripping away everything I had constructed.”
  • What is the single most important lesson you learned from this? – “Stop fighting and turn your triggers into prosperity. Looking at what is triggering you and why and how you can leverage that to start healing and help other people.”
  • How do you protect yourself from failing in this way again? – “Failure is a self-declared state. Failure and rejection are two very different things. If I fail it is because I say I fail. I don’t fail, I learn. If I’m rejected it forces me to look at changing my plan, which is still not a failure.”
  • Who do you turn to when you need help? – “I’ve a very small circle of friends that I know I can speak to about everything and my husband, I’m very vested in our relationship.”
  • What advice would you give to someone in a similar position? – “Simply: be open. You can let opportunity find you and think about yes you may have wanted to direct your life in a particular fashion that option is not possible anymore, so be open to what you can do.”

[28:10] Connect with Hilary at, an organization dedicated to providing support, resources, hacks, and hope to entrepreneurs affected by chronic illness, pain, disability, and sickness.

[35:30] Hilary’s final thought: “Keep going. Don’t overthink your actions, remember that imperfect action is better than standing still in doubt.”

To hear this episode and many more like it on your mobile device, you can subscribe to How To Lose Money via iTunes or Stitcher.


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