Plot Your Course
Career design for web professionals
with your coach, Whitney Hess

Who is driving your career?

The days of the career ladder are long gone. While our parents dutifully stayed at their jobs for 30+ years, now even 5 years at the same company can feel stifling. Why? Because the world is moving faster than ever before; societal change is happening at a breakneck pace; technology is transforming what it means to be human; and we have more information at our fingertips than ever before in human history…combined.

No wonder we’re so dizzy!

The web is still so new and constantly evolving. At only 25 years old, careers in technology are totally unregulated and vague. It’s no surprise you’re struggling to figure it all out. I did too! Until I finally realized the truth about the tech industry.

There is no career path. You get to design your own.


Plot Your Course is for you if:

  • You feel like you’ve plateaued and don’t know what challenge to tackle next
  • You’re hindered by a corporate culture that isn’t conducive to great work
  • You feel like something is missing and you just don’t know what it is
  • You’re desperate to do work that matters and make a difference in people’s lives
  • You’re scared it may be too late to “start over”
  • You’re not sure anymore if the work you’ve been doing is what you’re meant to do

You are the captain of your own ship. Let me be your navigator.

You don’t have to do this alone, but you do have to take command. It’s time for you to do what all the people you admire in this field have already done. We’ve make our own rules. Let me show you how.


Kaitlin MaudCoaching with Whitney has helped re-frame my perspective on myself and my skills, and find new excitement in my unique offerings. This has helped build my confidence in work, and really all areas of my life. Read more >
Kaitlin Maud, Los Angeles, CA


Plot Your Course participants have:

  • Developed new skills
  • Sold their best ideas
  • Earned greater responsibility
  • Taken on paying side projects
  • Received praise from coworkers
  • Been offered speaking gigs
  • Found their mentors
  • Redesigned their portfolios
  • Entered grad school
  • Launched to rave reviews
  • Earned raises and promotions
  • Found more meaningful work


I have spent the last decade building a career in technology, from being an interaction designer at a digital agency, to a user experience strategist at a financial software company, to running my own consulting business since 2008. I love what I have created for myself and I want you to feel the same.

Your most important project is you. I want to show you how to use the principles and methods of UX to design your own career.

When I was three years out of college and unclear what was next, I asked my boss at the time what my career path was supposed to look like. “I don’t know what the career path in this is,” he said, “but whatever you do, don’t follow mine.” Scared and confused, I slowly got involved in the UX community, looking for guidance and inspiration. By observing the careers of others and asking a lot of questions, I began to map out my own desired trajectory.

Now seven years later, I’ve gone from a full-time wireframer to a certified professional coach, from designing interfaces to designing companies. When you Plot Your Course, I will share the stages of my professional evolution — how I decided what each step would be, how I made it happen, and what is coming next — and show you how to use the same techniques to design your own career.


Aleatha SingletonWhitney’s coaching has literally changed my life. She was able to dissuade my doubts about my career choice, worked with me to set clear goals and encouraged me to overcome my fears and take more chances in order to design my own life. Read more >
Aleatha Singleton, Houston, TX


When you Plot Your Course, you’ll receive:

  • A 10-week intensive program to design your own career in tech
  • Weekly 1.5-hour group sessions via web conference to dive deep into each exercise
  • A comprehensive workbook for you to get messy and start plotting now
  • An mp3 guide to walk you through every exercise in the workbook
  • 2 private 1-on-1 coaching sessions with Whitney to amp up your progress
  • Your own buddy, a fellow plotter to lean on throughout this process and beyond
  • Recordings of all group and private sessions
  • A private group forum to get feedback, support others, and connect with likeminded web professionals designing their own careers

The 10-week program will follow this timeline:

  1. Career Objectives: What do I want my legacy to be?
  2. Target Audiences: Whom do I wish to serve?
  3. Problem and Purpose: What is the purpose of my work?
  4. Success Metrics: How do I want to define my success?
  5. Scope Assessments: How competent am I within each domain of business?
  6. Growth Roadmap: What does my ideal trajectory look like?
  7. Functions and Capabilities: What skills will I need to develop long-term?
  8. Phased Development Plan: Which new skills will have the most impact now?
  9. Marketing Plan: How can I get the right attention from the right people?
  10. Daily Habits: What is one thing I can start doing today to make a positive change?

The next Plot Your Course program begins May 8, 2015

Group sessions will be held via live web conference. All sessions will be recorded.

  1. Friday, May 8 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  2. Friday, May 15 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  3. Friday, May 22 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  4. Friday, May 29 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  5. Friday, June 5 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  6. Friday, June 12 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  7. Friday, June 19 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  8. Friday, June 26 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  9. Friday, July 3 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT
  10. Friday, July 10 at 12:00-1:30pm PT / 3:00-4:30pm ET / 7:00-8:30pm GMT


Are you ready to Plot Your Course?

Registration is now open, and closes at 11:59pm PDT on Wednesday, April 29.

P.S. If you don’t love it, it’s free.


While the three info sessions have already passed, Whitney is happy to answer any and all of your questions about the program. Enter your contact info below and Whitney will be in touch shortly.

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Colleen BeatonI’m thrilled that I was able to be a part of this with you. I’ve gained so much from our work together, there are no words to say just how appreciative I am for all of your guidance and wisdom. Thank you so very, very, very much. It really is an honor to have you as my coach. Read more >
Colleen Beaton, Boston, MA