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Rebel Advisors James Wightman & Kristen Cruz on Having the Right Conversations, Research and Self-Reflection, and Multiple Right Answers – Cracking Creativity Episode 38

James Wightman and Kristen Cruz are the co-founders of Rebel Advisors and the authors of The Rebel Way. They want to show students that college isn’t the only path towards success. In this episode, they talk about how conversations can lead to more informed decisions, how research and self-reflection can put you on the right path, and why there isn’t just one right answer in life.

Here are three things you can learn from James and Kristen:

Conversations Can Help You Make Better Decisions

The problem with most students who go to college and don’t finish is, they never stopped to think about what they wanted out of the college experience. They are told by their parents and counselors that college is the path they need to take. They are never given the chance to decide for themselves whether college really is the best path.

That is why conversations with those who want to help you are so important. These conversations can help students identify the paths they can take, find something that makes them comfortable, and build the skills they need for what they are seeking. They can help you find the motivation necessary to find what lights you up inside.

Finding the Right Path Requires Research and Self-Reflection

It can be hard to find what you want to do with your life. The majority of college students change majors at least once and only 27% get their first job in their given major. That is why it is so important to do research and self-reflection before you choose a path.

James begins the process of helping students by doing research. He sees what options align with the skills they have. Then guides them towards something where they can use those skills.

Kristen begins with self-reflection. She has the student figure out what they want first before she can begin to help them. It is only when you know what you want that people can help you get there.

By doing research and self-reflection you can align your skills with what you want to do. These things will give you a better idea of what you should pursue in life.

There Isn’t One Right Answer

One of the main problems with the education system is, we have taught people that there is only one right answer in life. Schools teach for the test instead of the process, and it has stifled our ability to be creative.

This has led to a society of people who are afraid to make mistakes. But mistakes are where you learn the most.

The thing is, you shouldn’t try to fail. Failure in itself isn’t the goal. It’s the lessons that you learn from failure that are the key to success.

One thing to consider is finding something you want to do, even if you fail at it. What thing are you willing to take risks for? What has a strong enough pull that you are willing to let go of fear?

Pursue that thing without fear of consequences and you will no longer look for the single right answer. You will try and try again until you’ve found the path forward.


  • about Rebel Advisors
    • looking to create alternative paths and challenge the typical college path to find more ways to success
    • both worked at the same university and noticed trend of creative students struggling with the traditional path
      • they didn’t know where they wanted to go
      • wanted to pursue a path not supported by education
  • Kristen’s path to Rebel Advisors
    • grew up with entrepreneurial and creative father
      • talked about business
      • challenged her to do something different
    •  first to graduate college
    • likes to solve problems and challenge what was
    • took alternative path after realizing she was different
    • studied industrial and organizational psychology
    • met James at careers services center at University of New Haven
    • they asked themselves what’s going on, realized it wasn’t for everyone
  • James’ path to Rebel Advisors
    • was into music when he was younger
    • worked with a guidance counselor and decided to go to college
    • bachelor is music industry, realized he just enjoyed music
      • stuck with the degree b/c it was easy
    • realized he enjoyed working with others and helping them
    • noticed other students were like him, didn’t know other options were available
    • they want to create other options because counselors tell them they need a degree
    • no one looks out for the students
  • conversations that stood out before they formed Rebel Advisors
    • wasn’t just one conversations, but multiple conversations
    • ran into students at different levels saying they didn’t know what to do
    • you don’t need to follow the path others set out for you
    • Kristen remembers faces and seeing worry
      • man studying music because parents told him to, not because he wanted to
    • Kristen and James talked a lot about life and helping others
      • centered on going to college
      • they didn’t see other options
      • heard statements like “I don’t know what to do, but this is what I’m going for.”
      • college is built for something in particular
      • aiming for entrepreneurs and creatives

“If you’re on that road where you’re studying business… or a degree that’s going to lead you to a job that has been defined for you… that’s a well established path, that’s okay… but if you’re really a creative and you’re looking to push limits or do something that’s never been done before… you might not find that in a university setting.

  • what they would do if they didn’t go to college
    • James – would be doing something similar
      • everything he does is aimed toward solving a problem or helping others
      • “Really, I find that, no matter what I do… everything’s about solving a problem that I think needs solving.”
    • Kristen – would have gone into family business
      • helped dad with international marketing when she was young
      • might have been a dancer
      • something creative
  • how they help others make a decision on whether to go to college
    • starts with a conversation of what they’re looking for
    • going through the filler that other people put in their minds
      • if you don’t go, you won’t be successful
    • they base their decisions on what people say not what’s going on in their head
    • identifying paths, finding something that makes them comfortable, and building the skills they need for what they’re seeking
    • identify what your motivator is
    • it’s okay to find an advisor
    • find your driver, not necessarily what your parents are telling you
    • if you don’t listen to yourself, you’re going to eventually come to the realization that you aren’t in the right career

“It all starts… with really the discovery process of what is it that they’re seeking, how do they want to be fulfilled, what are the things that make them happy, and then ways that they can pursue that.”

“Really, one of the main drivers for my conversation is to listen to your inner voice. That if you don’t take time to reflect on what it is that you want versus what society is dictating you to want, you’re missing out on what’s going on.”

  • high school students looking to go to college and people who want to change their jobs
    • in both cases: it’s people seeking something different
    • those being pushed vs. an unclear path b/c they didn’t listen to themselves
    • no system set up for people to figure things out
    • less stress for people looking to go to college
    • when you’re mid career, you might have children or other obligations
    • you must ask yourself “What is it that’s going to be in line for you and what’s next?”
    • people are seeking things that will fulfill them externally, but not internally
  • questions they ask people who are having trouble
    • guy came told Kristen, he felt he should get MBA
      • she asked where it’s coming from, and why he’s doing it
      • based on skillset
      • what skills do you have, what can you bring to the table?
      • what are you bringing and what’s leading you to pursue it?
    • James is more blunt with people
      • solving puzzles and challenges
      • asks simple questions to get people to connect the dots
      • going for a job posting, but not knowing what skills are necessary for it
      • being good at something but not liking it
      • ask probing questions to find out why they are making a decision
  • steering people towards what they want to do
    • James begins with research
      • see what aligns with their skills
      • how do they want to use and package their skills
    • Kristen thinks it has to do with the person
      • be alone in reflection, then figure out next step
      • sometimes people expect you to give them the answer
      • being an accountability partner to figure out what they want
    • putting together group of coaches for people to explore their options
    • alternative options – travel and explore
    • creating services because they aren’t available at college or they cost too much
    • education system doesn’t teach you to find out what you want to pursue
    • institutions aren’t looking out for students
    • students don’t have resources they need
    • before college/during college is the time to explore and create a life in line with they want to do

“Sometimes people don’t realize, but taking a step back from your everyday life… it really can help you gain perspective.”

  • difference between Rebel Advisors and advisors at college
    • Kristen
      • candid conversations with individuals
      • tailored towards creative people
      • universities want control
      • want to reach out to people who want to do something new/challenging/want something different
      • being supportive and letting people know they are in charge of their own future
      • you should be excited and energized about what you do
    • James
      • the risk of saying something that can get him fired
      • believes in being honest with students and treating them as people
      • getting to know people and having candid conversations
      • the risk of being looked at differently
      • impacting students in the best way that’s in line with them
  • changing the way people view college
    • Kristen
      • she’s on talent side, he’s on education side
      • research shows that there are organizations and institutions trying to make the change
      • ex: Google not needing a degree to be hired
      • organizations are agile and willing to change
      • want people who can think on their feet
      • not enough entrepreneurial systems within education
      • organizations partnering with them for alternative path mindsets for creativity and entrepreneurship
    • James
      • email them at if you are interested in partnering
      • the need to transform the way people hire based on skills/experience and not college
      • colleges have to get back to what they do best: education
      • the single lecturer and writing paper method being outdated
      • Alan Watts method – educating people for the future
      • to change perception of college, they need to change what they’re doing

“Create the results that you want in your life, and that’s the best way to learn, through the process not through someone asking to digest some information.”

  • how they would change education system
    • James
      • make it less systemized
      • focusing on results a person gets to show they are learning
      • Agile learning – less about learning content and more about getting people engaged in process of learning
      • learning is divided by generations
      • pursuing what they want
    • Kristen
      • giving the open space for people to thrive, less rigidity
      • institutions with white walls and sterile look
      • where would they be without desire to be creative?
      • fostering creativity, uniqueness, and being different
      • World Domination Summit
      • inspiring instead of giving people directives and strict rules
      • what is the environment? are people just being spoon fed information?
      • you don’t get a grade in entrepreneurship
      • looking at environments and opportunities in new light

“In order to be creative, you have to have creative environments, and when you don’t have that all you are doing is stifling what could be.”

  • changing educational environments to foster creativity
    • James
      • stop engaging creating programs to engage students but treat them as people instead
      • work with students to learn instead of spoon feeding them
      • creating results they want in life
      • let go of tradition, get rid of white walls, and  let the creativity out
    • Kristen
      • get students involved and ask them what they’re looking for
      • get feedback from people who will actually be involved
      • ask questions instead of making assumptions
      • sometimes educators think they have to have all the answers, and that’s not the case
      • foster learning and be a facilitator instead of being the expert

“We should really just stop and take a moment and say hey… let me get your feedback on this or can we collaborate or what do you think would work… and after something has been implemented, ask them what do you think went well and where do you think we can improve because the answer’s right there and I think sometimes you miss that.”

  • single answers of the education system vs. multiple answers in life
    • James
      • people are afraid to fail and make mistakes, but that’s where we learn
      • when you don’t make mistakes, you end up where you don’t want to be
      • Go For No  by Richard Fenton
        • most people are trying to get people to say yes, but you should do the reverse because it will make you more resilient
        • creating a personalized path
    • don’t just fail, but learn from it
    • Kristen
      • Daring Greatly by Brene Brown
        • what’s worth doing even if you fail?
        • people are afraid of rejection factor
        • taking risks and letting go of fear
      • cognitive dissonance – what you do is different from what you believe
        • you want everything to match up because it helps you succeed
        •  let go of the fear
  • lessons from their book: The Rebel Way
    • going to college route vs. the detour
      • actions that can lead to success
      • success is defined by the individual
      • book has guidance, but they aren’t giving a road map
      • what you can do in college vs. what you can do outside of college
    • making the decision
      • you have to make your own decisions
      • people are looking for the answers, but the answers are inside you
      • book is meant to be a tool to help you figure out what’s right for you
      • giving people the resources they need
      • if you are going to college, how can you do it differently?
  • determining if you should go to college
    • “I think it’s more about pursuing what you want and seeing what comes of that.”
    • if you are going to college, there is a particular purpose otherwise you are getting a degree for a job you might not want
    • Kristen
      • took time to research what she wanted to do
      • a lot of times people view college as a promise (higher pay, dream job, etc.)
      • you have to consider your path
      • she started her own jewelry business in high school but flopped
      • didn’t go to school to be an entrepreneur but did start businesses
      • sometimes you just have to try things
      •  if you don’t have a plan you could be wasting time, money, and resources
      • people pursuing school to avoid life (school addicts)
      • does it really make sense?
    • people look at college as a promise, but don’t look at the results
    • most people go to college not knowing what they want to do
    • 80% change major once, 27% get job in field, average of $35k in debt
    • what’s really necessary?
  • day to day work of Rebel Advisors and the future of the company
    • building a community and connecting with people who believe in the same thing
    • finding ways to best serve people
    • constantly juggling RA and their full-time jobs
    • planning for the future
    • getting out the message that college isn’t the only option and isn’t the dictator of success
    • they want to start a massive movement
    • success being self-defined and people being unfulfilled
    • helping people define what success means to them
    • not becoming a corporate drone – running out of steam and going into auto-pilot
  • building community
    • crucial conversations and addressing the elephant in the room
    • let people know how they can get involved
    • building partnerships, being on podcasts
    • identifying ways to help
    • build trust and looking out for one another
  • favorite quote
    • Kristen
      • “What’s worth doing even if you fail?”
    • James – has them on his vision board
      • “Everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it… Once you learn that, you’ll never be the same again.” – Steve Jobs
      • you can choose what’s right or wrong
      • creating life, a movement, and answers
  • morning routine
    • Kristen
      • 2 challenges – loving sleep, and ideas coming in the shower
      • brainstorming during morning activities
    • James
      • hitting snooze button from being night owl
      • listen to music/work out
      • writing out thoughts
      • play music
  • books, tools, resources, etc.
    • Kristen
    • James
      • Startup from Alex Blumberg
        • challenges of creating a startup
        • good for people starting out
  • creative people
    • Kristen
      • her dad (entrepreneurial father)
      • being unique is okay
      • taught her it is okay to stand out and be different
      • taking risks and do something that aligns with your gifts
      • Marie Forleo – create business and life you love
        • creative, multi-talented, and had interesting path
    • James
      • finds the questions challenging
      • different types of creativity
      • needing to exercise your creativity
      • boss – academic dean
        • unconventional thinker that transforms education
        • comes up with different ideas
        • good at executing ideas
        • tap into potential of others
  • definition of creativity
    • James
      • exercise areas that need exercising
      • taking improv so he can go with the flow
      • develop strengths and manage your weaknesses
      • try new things
      • stepping up path you normally wouldn’t follow

“Creativity is just challenging the way you do things.”

  • definition of creativity
    • Kristen
      • bring something new to the table of value
      • more to do with action not thought
      • have ability to push boundaries and push through fear and see what comes out on the other side
      • have an impact on something greater than yourself

“I look at things that have to do with building something that doesn’t exist or fixing something that is broken or even pioneering change.”

  • challenge to audience
    • listen to your inner voice
    • the answer lies within
    • join a community of like-minded people

“You don’t have to always seek information outside of yourself to make you creative.” | Twitter

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