**Seeking Immediate Work in Rockville, MD area**

Jess Chan O’Donnell

Featured photograph taken by Adan Ramos Photography.

The Ambitious Among Us

The person behind the job.

Their ambition, their strategy.

Meet the amazing business and technology minds of the Vancouver-metropolitan area and beyond.


Photograph taken by Adan Ramos Photography

Sometimes, when you ask someone about her present, you get her past.  And, when you learn her past, you comprehend her present. That was the case when I interviewed entrepreneur, creative, industrial designer, Cactus Card Co-Founder, and Night Market Vancouver Owner / Manager, Jess Chan-O’Donnell.  Hers is a powerful story.

**A quick note of acknowledgement and thanks to those who gave permission to use their logos, research, reviews, online content and educational videos for this article.

Informational Interviewing Tip

Let’s start with a pro tip, shall we?

As can be found on my webpage, What Is An Informational Interview, I have a go-to question.  The purpose of that question is “to learn about the person behind the job. Let him or her define who he or she is as context for what he or she does, how his or her career came to this place, and above all, why this person does what he or she does.”  

My interview with Jess is a manifestation of why I ask that question.

Cultural Transition

Jess’s parents were first-generation immigrants; in tow with them were the underpinnings of Chinese culture.  Over time, and as Jess was a child growing up in the United States, she took on American culture. That clash of values was stark and meaningful and dreadful.

Cultural transitions and managing cross-culturally are the topics of research, academic papers and books.  It should come as no surprise that growing up was challenging.  Jess was naturally one way, and her upbringing continually pushed her in another direction.

A drawing Jess did called Phoenix shows off her great talent.

Cross-Cultural Tension

She was pressured to perform.  For example, academics were high priority.  Nothing but top marks were satisfactory. Jess felt under immense pressure to conform, too.  Among other stressors, Jess was the younger daughter in a more male-dominated culture, an artist in a family that wanted her to be a doctor or lawyer, and a free spirit in a household that demanded compliance.

And all the while, Jess wanted to make her parents proud.  

Down to her core this motivated her behavior and performance. Jess was all-everything – an excellent athlete, (having gotten her black belt at age 15), a damn good artist, the homecoming queen, honor roll and class president. Emotionally, she was conflicted.

Duality deeply affected her health, well-being, relationships, and so on.

Culture Comparison

Geert Hofstede, Ph.D. literally wrote the book on cross-cultural understanding.  In his seminal work, Culture’s Consequences, Hofstede introduced categories of national cultures, called dimensions (Jan Hofstede, 2019).  Ultimately, he defined culture as

The collective programming of the mind that distinguishes the members of one group or category of people from others.

Geert Hofstede, Ph.D.; Hofstede Insights, 2019

Chinese and American cultures are very different (Hofstede, 1993).  Factors such as equality, individualism, long-term orientation, and conservatism were apparent during Jess’s informational interview.  

Based on those dimensions and the larger body of Hofstede’s work, Hofstede Insights is a consultancy that offers a free cultural comparison tool.  The chart (at left) is a recreation of that tool’s comparison of cultures in China and United States.

The chart (above) shows among others the four dimensions mentioned earlier in distinct contrast with one another.  

Filtered and with a little more detail, the table (at right) shows the cultural hurdles Jess had to overcome.


The way you maintain the resilience of a system is by allowing it to probe its boundaries.

Brian Walker, Ph.D., Stockholm Resilience Centre, 2009
Video used with permission of Stockholm Resilience Center, and Brian Walker, Ph.D.

It took Jess a lot of hardship over years and years to begin probing her own boundaries.  She suffered from bulimia nervosa starting in high school. Leaving her home for college did not prompt healing in the short-term.  

Relationships, experimentation, some risk-taking and seeking help led to reconciliation with her family and, to a larger extent, with herself.  

Jess does not suggest that she as a person is a finished product. She’s enamored with the thought of “finding what drives you” and “being the best version of yourself.”  

Contrast such an outlook against from where she came, mentally, emotionally and psychologically. For that reason her story to date has a great ending.

Not Without Hardship

We normally speak to the movies or Hollywood as being unrealistic.  Sometimes the character-driven scripts take artistic leeway to test the character and let an audience see his or her arc.  Jess is real, and so too has been her life story.

Amid personal health issues, Jess suffered further still.  She lost two loved ones (a boyfriend and her grandmother that raised her) in the span of two years. Their nature–living life in the present, unconditional love, caring for Jess in ways others had not–served as a trigger when they passed.  

Self-acceptance – the ultimate equalizer and vehicle for individualism.

It took as long as what the professionals say–9 years–to completely cleanse her sense of self to the point where the bulimia is completely gone, an old episode of life.  (Author’s note: Jess, you rock!)


After our informational interview, Jess wrote me. She asked if I could include one other point about her recovery, a description that galvanized if not exceeded resilience.

Cognitive scientist and author, Denise Cummins, Ph.D., wrote about mastery and defined it as such:

Mastery refers to the degree to which individuals perceive themselves as having control and influence over life circumstances.

Denise D. Cummins, 2015

Soon after acknowledging her recovery, Jess worked as an instructor / personal trainer.  In so doing, she had an agenda. “Having understood how much of an addiction [bulimia nervosa] was, how detrimental and how much it consumed my own life, I felt a need to assure no one went down that same path if I could help them.”  

Not only that, Jess found that job reinforced assurances in her own mind that she was healthy again.

She is constantly moving forward – truly “the ambitious among us,” as is the moniker of ‘Interviews of the Ambitious’!


Entrepreneurship is sometimes referred to as a calling. In a way, that appears true with Jess. She craves the freedom associated with creation, creativity, solving problems, and bringing together disparate groups. Mostly, though, “what really motivates [her] is knowing [she] can make an impact on someone in a positive way.”

The ties to her upbringing are apparent, and yet healthily pertinent. For instance, performance, conformance and making her parents proud have evolved. The energies once used to adhere are now a means to positively influence others. Influence is power. In that way, Jess is a power broker.

Great Life Mentoring

Logo used with permission of Great Life Mentoring.

Jess gives back in an exceptional way.  Her life experience growing up affords her a deep, special empathy for those with promise and potential.  

For the past 5 years Jess has mentored a talented and becoming young woman who, by the sounds of Jess’s description, is a pretty amazing individual in her own right!

For more information about Great Life Mentoring, click here or on the organization’s logo (at right).


WINKPEN, a Modern Human Instruments product, was a dignifying effort in her mind for going for broke.  Jess nearly did – and the product was amazing. It was her first major venture into entrepreneurship.

The result was particularly fascinating for two reasons.  First, WINPEN was a successfully-funded Kickstarter project.  Then, secondly, Jess knew nothing about fountain pens nor the fountain pen community before she started.  (We can be a discriminating bunch.) And, the writing instrument had a glass nib – a polarizing feature given its inconsistent writing experience, production standard, and inability to be easily altered by the pen’s owner.  Jess cared for every order so her customers would “feel loved.” Full disclosure, I am a customer and can attest!

And the love was bestowed back upon her.  SBREBrown, perhaps the fountain pen community’s foremost online reviewer and influencer (and one of my favorites), reviewed the pen and had some rather nice things to say (Brown, 2016).

Video used with permission of SBREBrown (Stephen Brown).

Freedom Forward

Nowadays Jess is focused on what freedom from conflict and constraint provides.  Before she and I sat down, her identity to me was a successful, local entrepreneur.  She doesn’t deserve labels. The fact of the matter, though, is that she really is a terrific entrepreneur.

The difference between her past and how I as a random person accept her in the present seems to me to be how she, as Dr. Walker said, “probed her boundaries.”   She seems to have gone back to her past, becoming the person she was born to be.

Inspiration for this conclusion came from a video I saw of the famed social media and marketing guru, Gary Vaynerchuk (a.k.a. “GaryVee”).  He videotaped a conversation of himself giving business advice to a young businessperson. Vaynerchuck’s insight was profound. He said

You know it’s funny.  Right now I can say ‘you should’ because I’ve built so much.  But if I was at 20 it’d need to be like ‘my intuition says’…and that changes everything.

Vaynerchuck, 2016

Jess’s intuition is breaking through.  She’s free.

About Night Market Vancouver

A community event featuring more than 80 local vendors, this monthly attraction is one for the family to enjoy food, music, entertainment and lots of shopping.

The next Night Market Vancouver takes place March 22 from 5-10p at Terminal 1 / Warehouse 23 (see map below).

About EcoBots

Jess turned technology and robots and the future into a sustainable gesture.  “A small little venture out of [her] very own home, [Jess] created and handmade EcoBots for a little while in between her business ventures.”

The purpose for the handmade, 3D-printed figures made of biodegradable plastic was to “stop and remember to give back to the planet we call home.”  Each EcoBot came with a small ‘air’ plant as hair on their heads, and, for every EcoBot purchased, a tree was planted courtesy of Jess’s partnership with One Tree Planted.

Jan Hofstede, Gert. “Geert Hofstede | Biography”. Geert Hofstede, 2019, https://geerthofstede.com/geert-hofstede-biography/. Accessed 23 Jan 2019.

Hofstede Insights. “Our Models – Hofstede Insights”. Hofstede Insights, 2019, https://www.hofstede-insights.com/models/. Accessed 23 Jan 2019.

Hofstede Insights. “Country Comparison – Hofstede Insights”. Hofstede Insights | Country Comparison Tool | China, United States, 2019, https://www.hofstede-insights.com/country-comparison/china,the-usa/. Accessed 20 Jan 2019.  Chart manually recreated.

Hofstede, Geert. “Cultural constraints in management theories.” Academy of Management Perspectives 7.1 (1993): 81-94.

Cummins, Denise D. “Why Some People Are More Resilient Than Others”. Psychology Today, 2015, https://www.psychologytoday.com/us/blog/good-thinking/201503/why-some-people-are-more-resilient-others. Accessed 3 Feb 2019.

Walker, Brian. “The Best Explanation To Resilience”. Youtube, 2009, https://www.youtube.com/watch?time_continue=16&v=tXLMeL5nVQk. Accessed 20 Jan 2019.

Brown, Stephen. “Wink Pens Glass Nib Wink Pen | Hey There! SBREBrown”. SBREBrown.com, 2016, https://www.sbrebrown.com/2016/09/wink-pens-glass-nib-wink-pen/.

Brown, Stephen. “Wink Pens Glass Nibbed Fountain Pen Review”. Youtube, 2016, https://www.youtube.com/watch?v=yJ-EDKesnjU. Accessed 23 Jan 2019.

Vaynerchuck, Gary. “Advice To A Young Man That Many Of You Need”. Youtube, 2016, https://www.youtube.com/watch?v=HwXsFPZp3fQ&t=993s. Accessed 20 Jan 2019.

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Some have called me an expert at informational interviewing. What does that mean, exactly? I am concerned with understanding the whole person, the people behind the job, and the whole business from within.

It should come as no surprise, then, that I support the ambitions of others to meet promise and potential

My MBA is concentrated in Strategy. I have 20 years of work experience, most of which is in the field of organization development. Conducting informational interviews, I have engaged local professionals and written research-backed articles about their ambition. 

Writing is fun, and so is sharing what I learn. I’ve given talks throughout the Portland-metropolitan region about informational interviewing, and more recently about scaling-up ones activities – recognizing one’s current resources and opportunities, and then pairing them with potentially new resources and opportunities through creativity, new possibilities and strategic fit. 

I am heavily involved in the community, and I love coffee and fountain pens!

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