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My Life Is A Caricature. Is Yours?

My Life Is A Caricature. Is Yours?

Here’s an up-close and personal view of a whole life in a few dozen bullet points. For entertainment purposes and accuracy, I’ve highlighted the most significant, most formative experiences. Rather than tone down them down, I’ve maybe even dressed them up a little. In relief like this, my life is a caricature.

Not everyone will be proud of me for publishing this for the world to see. I have spent much of my life suffering in silence and protecting the secrets of others. Secret-keeping is the foundation of abuse in all its forms. “Don’t tell anyone.” “Just sign this non-disclosure agreement.”

Perhaps discretion is the better part of valor, but for what? Many kept secrets hold no value, either in the world at large, to the people whose secrets are protected, or to the people holding the secrets. Often, secrets shield abusers from accountability, and they create more victims when the abuser continues a form of behavior they desperately need to change.

I’ve learned the highest value to the world and me will be revealed when I authentically express my true self—no more hiding. Facts are facts. This exercise is therapeutic.

In the end, this will help far more people than it hurts. That is my intention.

My Life Is A Caricature


  • As the first of 3 boys, I realized at age 28, I have blind spots about women. I grew up with no sisters.
  • I had survived my first divorce by age 2.
  • My parents were an only boy (youngest of two) and the youngest girl of 9 natural siblings who also grew up with four nieces as ‘younger sisters.’
  • In 7th grade, I helped my Mom through Nursing school by tutoring her in Algebra.
  • By middle school, my second divorce was well underway.
  • When I was 16, my Dad fired my younger brother and me. “Do you even want to be here?” “No,” said my brother. “Get out of here! You’re fired,” my Dad fired back. That was that. In retrospect, this was the beginning of him fulfilling his commitment to raising us to 18 but no further. He had done his part, and there was no future for us in his company.
  • I worked two more summers with my Mom’s boyfriend’s much larger construction company, Super Structures. One fantastic summer, we built the initial concrete foundations and post-tension concrete garages for Cupertino City Hall. What an excellent experience. 
  • My high school swim coach always laughed at me: I was his first athlete who’d ever missed swim practice because I had a meeting with my CPA. I miss Coach Crocker.
Dylan and Yancey with Age Group Swimming Trophies
I wasn’t a particularly gifted childhood athlete, and mostly I just swam, but I became a successful age-group runner in middle age. You can, too!


  • I earned entry to UC Berkeley through affirmative action. In my application essay, I wrote I wanted to help my Dad expand and grow the business. My Dad had other ideas.
  • Six years to graduate college. Five years of Fraternity leadership, including Lodge Manager, Treasurer, and President — twice.
  • While I was in college, the Clintons were in office, and media advised Social Security wouldn’t be around when I was old enough to collect. Motivated by the horror-media during the 1992 presidential campaign cycle, I determined to attend grad school while still an undergraduate.
  • I became first in my family to earn a Bachelor’s degree.
  • Later, I was first in my family to earn a Master’s degree, and I went to graduate school because life with a liberal arts degree seemed untenable. I went to grad school to learn how to invest my money, which is why I picked up a concentration in Finance. While there in Silicon Valley, it seemed right to pick up two more concentrations in MIS and Management of Technology and Innovation. A finance professor, Meir Statman, said the best portfolio is no-load index mutual funds. If you have the nerve to do it, he’s right.
  • I was first in my family to take on $115,000 in student debt. That debt will continue to amortize until I’m of legal retirement age.

20s Were Difficult

  • I lived on $14 a week for almost a year after I graduated college. Accidentally lost 50 pounds. I looked in the mirror one day and noticed I was scrawny.
  • I survived my first corporate acquisition when AiC acquired DPI. While the purchase was underway while I was interviewing and during the hiring process, they notified me during my first week on the job.
  • I graduated from grad school and changed careers from staffing/recruiting/temporary human resources services to software publishing. Among other things, I concluded in graduate school that software publishing is a highly desirable business model.
  • I spent 3 1/2 weeks in Buenos Aires, including a weekend at Iguazu Falls. While there, I took a course in International Finance.
  • I became a consultant and project manager when my boss suggested it. After only four months in that, my first ‘full-time’ job after grad school, the company laid me and 30% of the staff off, two weeks after telling the company it had been a great year.
  • I paid off the student loan my Mom took out on my behalf.
  • I started a business, then puzzled for 20 years why I had difficulty sustaining and growing it, even with an MBA.

30s Were Difficult

  • I raised money from friends to start a real estate investment business with family. Ultimately, I killed the company and returned the money. We spent a couple of months discussing new investment models every week but never following through on any one of them. It was clear we had more desire than the resources required to fulfill the original intention or the promise to my investors. My choice angered one of those family members, but it was the right thing to do.
  • Arrested in my front yard and went to my first AA meeting because my attorney suggested it. I didn’t read the book or get a sponsor. Also, I took six months of mandatory alcohol education, paid fines, and did several days of community service.
  • I spent four years as a traveling consultant, including six weeks in Mexico. Avoided travel jobs twice before, and finally couldn’t avoid one. Is it true that what we resist persists?
  • I took a 60% pay cut and moved halfway across the country after the dot-com bubble. I narrowly avoided bankruptcy by borrowing from family members to refinance credit card debt. Several years later, repaid in full with interest.
  • I earned the PMP project management certification.
  • I enjoyed my second corporate acquisition. Oracle created real leadership and momentum to move everyone forward in the same direction.
  • I became a lifetime member of AAII.
  • Left consulting and went to work in-house on a highly successful web property. I loved it, though we lived every day in the shadow of a previous, incomplete corporate acquisition.
Dread and failure are created conditions. You can just as easily create aliveness and success.
While my career was working reasonably well, I was feeling stuck, both at work and home.
  • I became coachable and got on the road to stop suffering.
  • I was nearly arrested a second time and went back to AA because I knew drinking would destroy me. There, I got a sponsor and read the book with him. I am grateful for Jay’s time and attention.
  • During this time, I divorced a wonderful woman I never married.

Things Began Looking Up In My 40s


  • Studied phenomenology at Landmark Worldwide.
  • CISSP information security certification.
  • I got a leadership coach: I owe Cookie my whole life.
  • I studied communication and leadership at Toastmasters.
  • ‪If one oversimplifies conclusions from social psychology experiments on people who share some of my genetics, one can conclude I’m a slow learner. Still, at least I have a high pain tolerance!‬
  • Lori and I, Larry and Debbie, and several other adventurous souls spent an amazing two weeks in Cusco, Macchu Picchu, Amazon rain forest, and jungle 4 hours by boat from Iquitos Peru. What an incredible series of experiences!


  • I got a nutrition coach. Carly opened my eyes to what’s possible, not only in nutrition but also in hiring professional services generally.
  • I spent some time in WeightWatchers. Karen is a brilliant and enthusiastic representative of the company and a lifestyle.
  • I lost 50 pounds the second time, and I’ve kept it off for five years and counting. My weight record, since I got my second weight loss rolling, is on MyFitnessPal.

Physical Fitness

  • I developed horrible sinus allergy symptoms, started taking allergy meds like candy, got diagnoses for several environmental allergies, then my doctor diagnosed me with autoimmunity (rare for a male).
  • After committing to triathlon and reading Phil Mafettone’s book on endurance training and racing, I got serious about athletic competition, diet, stress management, and sleep.
  • I hired a running coach. Steve and Chris have been inspiring, enthusiastic, and knowledgeable guides through both physical training and race execution. An amateur athlete could ask for nothing more. The journey has been unpredictable, incredibly difficult, and rewarding beyond measure or description.
  • Ran five marathons, several triathlons, and obstacle course races, and I’m just getting warmed up!
  • I had a very unpleasant inguinal hernia resolved through open abdominal surgery. Thank goodness! Hernia repair recovery was notably similar to marathon race recovery.


  • Finally, I realized Finance and investment knowledge isn’t worth a damn without money. Ha!
  • Lifestyles Unlimited taught me a great deal about investment real estate acquisition and operations.

Where I’m Going

Answers To The Big Questions

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About me
Dylan Cornelius
Dylan Cornelius

Hi, I'm Dylan Cornelius.

I help mid-career knowledge workers and entrepreneurs execute their strategic plans using the career acceleration blueprint, even if they don't know where to start, they've never been a manager, and don't have a team. I'm the creator of the Career Acceleration Academy.

I've led small and large collocated and remote teams, delivering more than $40 million in revenues and cost savings. My teams and I have delivered ground-breaking products and services that still power successful businesses today.

I've worked as a recruiter, manager, and team leader in Silicon Valley and around the world. I have more than 30 years of experience in business management and leadership, plus psychology and business degrees from top universities.

I'm glad you're here! Take a look around and let me know what help you need.

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