American Dream U

Going through the transition from one path in life to another (an inflection point) is stressful and daunting. I know – I've done it many times. I won't re-hash my story, you've heard a bit of it on stage and (if you're interested) you can learn more about my story here.

Instead, this page is a resource to help you, by sharing some of the insights I've gained going through mine and details I didn't have time to cover in the speech.

Oh – and before I forget, you're always welcome to reach out to me with questions. The best way to get a fast answer is via Twitter: @chrisplough.

[Note: I'm going to continue updating this page each time I give a speech with new resources I come across. Check back regularly for the latest. –Chris]

There are many paths

The first step is to realize that life is ever-changing. You'll likely take many paths and the ability to learn and adapt is one of the most important skills you can foster. This also means that you may take different roles at different points in life.

I've been an student, an employee at a “standard” job, been an intrapreneur, been an artist and also an entrepreneur. I don't consider any of those better than another – they were just right at the time. Being an intrapreneur was great – I got to learn a ton of new skills, all without the risk of starting my own business (and – with enough spare time to pursue other interests). On the contrary – being an entrepreneur has ultimately given me more freedom, financially and otherwise. The downside, especially in the beginning, is that it's all-consuming and came at the cost of time with friends and family. Ultimately, I learned skills and lessons on each path in life that made the next one more possible.

So – when someone tells you that you must take a certain path; step back and figure out what's right for you. Maybe you're at a point where understanding yourself or spending time on relationships is most important. Maybe a “normal” job where you have plenty of free time is best. What if you want to eventually start your own business, but don't know where to start? Then maybe it's best to join someone else's startup and help them achieve their vision. You can learn from their experience and also grow the network you'll later need to succeed. Maybe you are ready to strike out on your own and want to commit everything in order to succeed. Great – then fucking do it!

My process

Really, this is pretty simple – just the logical path I think through when figuring out the path I should follow. I like simple, especially when you're in the middle of a transition. When you're feeling mixed up and it's hard to tell the up from down – simple is our friend.

My thought process:

  1. Ask yourself hard questions
  2. Listen to your intuition for answers
  3. Validate with people who won't bullshit you
  4. Take action
  5. Repeat

What questions do I ask?

Again, I like to keep it simple. Here's what I focus on:

  • Have I learned everything I can from my current path (or – am I ready to transition)?
  • What impact to I ultimately want to have in life?
  • What is the next logical step?
  • What skills or resources do I need to make that become a reality?
  • What do I really want to do, which is within my reach, but scares me?
  • What is it that others need right now, that I'm the best person to provide?
  • What have I wanted to do, since I was a kid, but have been resisting?

How do I listen to my intuition?

I could write a whole post or book on this (and ultimately may). For now, though, the key is about being open mentally and emotionally.

During one of the hardest periods of my life, I was cut off from my intuition because I bottled up the grief of losing my parents. I pushed those feelings down so far that I became numb to the world and out of touch. It took a trek through Mongolia to finally shake things loose. Looking back, though, I didn't need to go to that extreme.

The key is:

  • Unwavering honesty with yourself
  • Creating the space for self-reflection
  • Talking with those you trust

Honestly with yourself is critical – both in being able to face what isn't going well, but also in celebrating the things that are. Too often we skew our view of ourselves.

Creating space for self reflection is simple, but also hard to master. Get away from distractions and give yourself enough space to truly deal with your shit. I do this in a bunch of ways – meditation, floatation tanks, traveling, trekking through nature, long motorcycle rides, working in the shop and talking with friends. Another option is therapy – though, I've avoided that most of my life (because I'm stubborn), but I'm coming around. Which ones work for you is a personal choice – so just keep trying until you find what works.

It's taken me years to get over the idea that “real men” don't talk about their fears and feelings. Now I believe there's a time and place to be stoic and simply get shit done and a time to open up with those that you trust. It's been a long journey, though, to accept this change and find people I could trust. Stick with it – ultimately it will also help you feel less alone, because you'll find that many of us share the same fears.

Where can you find people to trust for feedback?

When you've figured out the path you want to take, get unbiased feedback. You want those people who you trust enough to share, but who will give you their honest opinion. As much as you may love your grandmother or spouse, they care deeply about you and may sugarcoat their feedback. Deep down, you likely know for sure.

Do you have a trusted friend – the one who always give it to you straight and is willing to call you out? Hopefully one who is level headed and also not overly critical? Talk with them.

This is also where mastermind groups rock! If you're an entrepreneur, groups like EO (Entrepreneurs' Organization) are a good start – though they're more business focussed than personal. The key is to gather a group of people who trust each other and are willing to give honest feedback. You should consider starting one with the people around you now – people who are going through the same transition you are.

Thank you

More than anything – I want you to be successful. You have given years of your life to support this country and I want you to find your next path in your life.

If I help, in even a small way, I'll be incredibly proud. I'm continually learning – so your feedback helps. What connected and worked for you? What didn't? Let me know on Twitter (@chrisplough), so I can make this page and message better for future soldiers. Thank you!

Additional resources:

These are some articles that I've found useful and you may as well: