Challenging your life’s creative vision with coaching.

In the past year, I’ve set out to create my own personal set of values, principles, and a vision to live by. This is Principle #1. Always be becoming.

I’ve always been a huge fan of the Grateful Dead and typically read or listen to anything they are involved in. I came across the term “Always be becoming” in an interview with guitarist and vocalist Bob Weir in GQ of all places.

His longevity, adaptability and continuous search to renew himself has been a big inspiration to me. So when I read those words. It stuck with me. In order to stay creative, stay relevant, stay personally motivated. I need to always be becoming…

I wasn’t exactly sure how I’d internalize those words and put them into practice. Then one day while reading the book “The One Thing” by Gary Keller I knew it was coaching I needed to seek out.

I never thought I’d be the type of person to hire a personal coach of any kind. I’ve always foolishly prided myself on my ability to figure things out. Get there on my own and do it myself.

Gary was talking about elite performers & athletes and how they’ll eventually hit their natural limits. Elite performers and people who want to be the best in the world at something don’t stop when they hit those limits. They seek out coaching and teachers to get them to world-class status.

Now I’m no professional athlete, but this is the one card I have to play. My life. Limits, perceived or otherwise will have to be overcome if I’m going to design the life I want to live.

Seek coaching to challenge your own life vision.

Creativity is a beautiful and essential aspect of our lives. Whether you are using your creativity as a means of self-expression, personal growth, or to generate an income. It will be the key to crafting a life that is truly your own.

To me, there is no greater design problem than the designing of your own life.

After a year of personal searching and contemplation about what I wanted next in my career and getting nowhere on my own. I sought out two very different coaching programs from two very different types of creative coaches.

Whether you are a writer, artist, designer, or any other type of creative professional hopefully you’ll see how having a coach by your side can open up paths and perspectives hidden from your own vision.

If you’re stuck being and not becoming, unable to tap into that wellspring of inspiration, or even if inspiration moves you brightly and you know what you’re becoming.

Coaching might be the key to breaking free from creative stagnation and helping to build that ladder to your vision.

I’ll share my experiences and lessons learned from those two programs below.

Reality Prototyping with Coach Kate Pincott

https://www.realityprototyping.com

I first heard about Reality Prototyping while listening to Chris Do’s The Futur Podcast. Her voice was really soothing and her calm demeanor while she and Chris did a mock coaching session sounded like exactly the voice I needed in my life.

Before I talked with Kate for the first time. I was planning on building up my freelance design client list in order to go out on my own as a full-time freelance remote product designer.

I was in the beta program for this course, so I can’t speak to the format that it takes now, but it was set up with weekly assignments and weekly group coaching calls with two other designers plus Kate in my instance.

Kate asked some really insightful and deep questions that got me thinking about my direction and how I’d make this a reality. The weekly calls and assignments were also really good at helping me shape my personal values, principles, and creative vision.

I have picked up a few freelance clients since my coaching program with Kate so I know firsthand that her program works. If you’re looking to up your product design game, go full-time remote or freelance, or simply hone your craft. I highly recommend scheduling a call with Kate.

Here is a list of lessons I internalized in Reality Prototyping

1. Victim or Victor - Choose.

   If you’re sitting around blaming others for where you are, you’re missing the perfect opportunity to reflect, learn and grow. Choosing to understand the role you play in the outcomes in your life will set you on the path to your vision.

2. Design or Be Designed.

   If you don’t have a vision, a plan, and a roadmap for your life. Someone else has a plan for you.

3. The Reality Prototyping Loop.

   What are the 1 degree turns I can make in life instead of rewriting everything all the time? Instead of making grand plans. Make small experiments instead.

   • Learn = Listen to your inner voice

   • Build = Visualize the 2.0 version of yourself

   • Measure = Practice in the real world

4. If it doesn’t challenge you. It doesn’t Change you.

   In order to grow you need to get comfortable with being uncomfortable. Everything you want in life is on the other side of fear. You can take the easy route, but it won’t get you where you want to go.

5. You don’t need permission to change.

   You’re an adult. You don’t need anyone’s permission anymore to be who you want to be. If you want to make a change. Make the change. No one can stop you or deny you becoming the best version of yourself.

6. An experimental mindset.

   It’s not that you’re incapable of doing something. You just don’t know how to do it YET. Experimenting will get you closer with each failure. Maybe you need to try doing less. Pick one thing and do it for a short period. Then let your natural curiosity tell you whether it’s worth continuing.

7. Action is the antidote to anxiety.

   If you let things build up and never act on them. It will eat away at your soul. When my anxiety is at its worst. I’ve been thinking and not doing for too long.

8. Visualization is a powerful tool.

   Having a clear vision and connection to who you’ll be in the future is something I’m trying to build a daily practice around. You can’t become it if you can’t see it.

   Visualizing my future self and family life gave me a surprise revelation and a new appreciation for the life we’ve already built.

   I realized that my goals and dreams look pretty similar to what I already have. I’m in the place I want to be. I have a loving family. I have most of the things I want.

   It’s really all about improving the things I care about and acquiring the skills that are going to fulfill me and deepen the relationships I care about.

9. If you are overwhelmed. You haven’t broken down the problem enough.

   This goes back to that experimental mindset. If you’re making any project into a big hairy monster. You’re going to avoid it. What’s the smallest experiment you can make that will lead to a desired outcome or change? Break everything down into small, digestible experiments, and have fun with it.

10. Your own life iS your greatest design problem.

    If I worry about what other people think of me. I’ll never have room to understand what I think of me. I’ve spent the last 20-plus years of my career listening to everyone but myself.

    I’m an empathetic person so I put other people’s emotions above my own and often don’t speak what’s really on my mind for fear of causing a negative reaction in someone else.

    What I notice is that I do a lot of things in life for the benefit or perceived benefit of others. Not to keep myself true to my own personal intentions or values but as a performance for others.

    I’m beginning to feel a lot less worried about other’s perceptions as I get a clearer vision of what I want as I know now I don’t want what I thought others expected of me.

Go check out Kate and her Reality Prototyping program. Tell her I sent you.

The Side Hustler’s Coaching Program with Coach Scotty Russell

While Kate’s program was fantastic and I highly recommend it for UX/Product Designers. I was still lacking focus, direction, and a vision for my creative future outside of freelancing or being an employee.

I know I can make a living as an employee or as a freelance consultant, but if I’m really looking to “Always be becoming” then that means designing a life I actually want to live. And that is a life creating my own products, my own art, and my own creative endeavors.

I first met Scotty Russell at the Creative South Conference in 2022. I kept up with his Side Hustler’s Perspective Podcast after that and loved listening to the calls highlighting his student’s successes.

I tried out a short 3-week program and workbook of his and was instantly hooked. I love Scotty’s authenticity and no-bullshit demeanor. He asks hard questions, listens, and keeps you accountable. Which is exactly what I needed.

I joined a much more intense 12-week program offered by Scotty with 5 other artists and designers trying to work out their own vision for their creative futures.

I can’t say enough about the program and the people I met. It was inspiring, challenging, and eye-opening.

Whether or not it was life-changing will be up to me to continue on the path of hiring my inner child to design my future self.

You can watch, listen or read about the experience on Scotty’s Podcast or you can read about the series of art I created during this program here.

Here is a list of lessons I internalized During the Side Hustler’s Program

1. Accountability is key.

   Having an outside voice to question you when you slip or slide off the path you’ve set is something I need in my life. Someone who is not related to you can ask the hard questions and shine a light on your decision making which those who love you probably can’t do.

2. Write your own permission slip.

   I talked about learning this in Kate’s class, but this one needs another reminder. Again, you’re an adult, if you want to make art or do anything else for that matter, you don’t need anyone else’s permission.

   You can’t let voices on social media or anywhere else scare you away from creating the art you want to create.

   Write that permission slip to do something out of the ordinary, to have fun, to experiment, or to fail. It will be alright. You have plenty of time to be serious and boring at your day job.

   If you’re just getting back into a creative endeavor, don’t compare yourself to those who’ve been playing the art game longer than you. They’ve been at recess for a long time. You’ve been in class.

3. Silence the Tyrannical Mind.

   Based on doing the work of writing stories from our childhood during the program. I realized I’d been chasing three types of freedoms in my life. Financial Independence. Time independence. And Location Independence.

   The biggest realization for me though was that the freedom I needed to be seeking was the Freedom from my own Tyrannical Mind. I was my biggest doubter, my biggest hater, my biggest critic, and my biggest bully.

   No external force has kept me from creating for myself or creating art these past 10-20 years. It was all self-inflicted. All those ideas I’ve had that never went anywhere. That’s all on me.

4. Don’t be afraid to invest in yourself.

   These coaching programs are not cheap. They shouldn’t be either. You need to feel the pain in order to make the change. Why not invest in you? Ultimately you’re the only person who’s going to feel the regret of unmet expectations for your life.

5. Too Busy = Not a priority

   If you’re too busy to do something. Then it’s not a priority and that is just fine.

6. Do less, but better

   Let constraints be your friend to unlock the biggest results. Know your one thing. Keep your eye on the ball and only do that One thing at one time. Success is in subtraction

7. Know your season.

   My Season = Aggressively Having Fun!

   Always keep these questions top of mind: What season are you in? What's your #1 focus right now? What's the #1 result you are trying to accomplish?

   When distracted by shiny object syndrome. Ask yourself what your priorities are and what are you going to remove if you follow that distraction. Does the distraction now become your main focus? If not, put it on the back burner.

8. Time-block Everything.

   Professionals Plan, and hobbyists wing it. If it’s not on the calendar. It’s not a priority. It doesn’t exist.

9. Embrace the hard middle

   Be in love with the mind fuck of the creative process. Idea inspiration is an endorphin and feels great. Recognition of a job well done is the same.

   It’s the middle of solving a creative problem that trips us up. In order to get past it, you need to treat the Hard Middle as the most exciting part of the creative process.

10. You need to show to grow.

    What’s the worst thing that’s going to happen if you share your work online? Failure? What does that actually mean? Quantity leads to Quality! Don’t be afraid to post those turds.

11. 1% is better than 0%

    Whether it’s mindset or strategy all we can do is make small steps each day. It’s okay if you can’t give your all today. Give something. Keep your eye on the prize and be patient. There will be times when everything goes wrong and that is okay, do what you can and plan tomorrow.

12. Let your inner child design your future self

    Would your child self be proud of the person you are today? Would they be excited by what you are doing? Are you excited about what you are doing?

    My children were never interested in what I did for work. Until I did this program and they saw me drawing, they became very interested. We even got to draw together on a few occasions.

    If your current career or job is scratching that creative itch for you. Maybe let that child inside take the wheel and see where that gets you.

13. Lead with the Dream

    That dreaded question. “What do you do?” I’d always start that answer with what I do at my job, but there really is no need to mention what you do for a living at all. If you lead with what you don’t want, you’ll get more of that. Why not lead with what you’re becoming?

    I think most other people hate this question as well. I have a doctor friend who never mentions to anyone that he’s a doctor. Because he hates the conversations that follow. Instead, he talks about music or anything else he’s interested in.

    Some alternatives you can ask in your next social gathering could be “What do you do for fun?”, or “What are the groups or activities you pay to be a part of?” You might actually learn who someone is and not just what they do for a living.

Conclusion

Without surrounding myself with other hungry, determined, and searching artists and the guiding voices of experienced, insightful coaches. I don’t think I wouldn’t have gotten to the amount of clarity I have in my life now and where I want to take it.

Going forward instead of “being”, I’m going to Ground myself in intentional work rooted in play targeted at a clear vision, with accountability, rest, and productivity systems built-in on my way to “becoming” more me.

Always be becoming…