Leaping Off a Cliff With Both Feet

standing on a cliffI tricked myself into it, actually. Once I did it, there really was no looking back. The ledge is far behind me now with no way back up. There is no exit route, no escape plan for me, and the only way out is to head deeper into the abyss.

One year ago, I declared myself unemployable. As much as I appreciated what the corporate world had taught me, I knew it was time to make my leap. I’ve talked many times about how the Universe answered my call. The corporate world showed me the door in the form of a pink slip, but instead of dread and despair, I found freedom… mostly.

Scary, Scary Freedom

I wasn’t mentally ready for that kind if push, not at that moment. I have a huge mortgage and a family to support, and the idea of being self-reliant right then was scary as hell, but I chose to dig deep inside myself and see the opportunity.

It was down there somewhere, right?

Of course it was down there, along with many other things. I just had to move some stuff around to see it.

I started my new freedom adventure by taking some free time and committing to spend more of it with my son. We had him in daycare 5 days a week, so I backed that off to 3 and he got to spend time with me and his grandma. Spending that kind of 1-on-1 time with him is irreplaceable. I can’t imagine ever going back.

I also switched my workouts from evenings to mornings. If you know me, my physical training is as much a part if my success method as my business training. Starting a day with that energy level makes the workday fly by, and I’m usually hyper-productive after. Evening workouts were good, but after a long day, they were difficult at times. Mornings feel much better.

The problem now (which isn’t really a problem) is that I painted myself into a corner. If I ever considered going back to a corporate life, I would need to change my life for the worse. I will not do that to my son. I will not do that to myself. However, I’m human, and susceptible to temptation.

I still wrestle with limiting beliefs, just like you

Many years ago. I subscribed to a newsletter that pushes new creative job opportunities in the action sports area. I dreamed of working for a company like Quicksilver or Billabong, hanging out with surfers, snowboarders and skaters. This email was my lifeline to that world, or so I hoped.

I was eager to get out of my current job, to try something new, and every day I would peruse the email offerings, but not once in 10 years did I apply to anything. Why? Limiting beliefs mostly: not valuing my own skill, not feeling cool enough to hang with the likes of these kids, or just too comfortable to try.

Jump ahead to today, where I’m living my dream, even if it is kicking my ass, but I’m still getting those emails. Why?

I con myself I to thinking I’m getting them to look out for creative friends looking for work, but the truth is I’m still looking for something “safe”. A week ago, a tasty job came through that update. It was an art director job that might have paid a decent chunk, and for a couple days I thought about applying. I told myself it would alleviate stress on my family, let us do things we hadn’t been able to, like travel and fix up the house.

I told myself I could do that and still manage this site and the podcast, placing less emphasis on the coaching. The job was also near my wife’s office, so maybe we could commute.

And right there, an alarm went off.

If I commuted with my wife, I would have to change my workout schedule, going back to evenings.

If I commuted with my wife, that meant my son would be in daycare full time, seeing more of them than he would us.

If I commuted with my wife, that would mean I failed on point #1 of my mission—to leave a legacy my son could be proud of.

I told myself I was unemployable because I could never see myself going back into a corporate environment, but here I was debating it, yet the unemployable side fought back. I altered my life in such a positive way, no corporate job could ever replace it. I leapt off the edge of the cliff with no rope, and the only way to go is further into the abyss, but now I know something I didn’t before.

The abyss may look dark, make look deep, and we assume falling down means we are failing, but the abyss is filled with wonder. If you’ve ever walked into a dark cave, or dived underwater further than anyone else, you know that secrets lie in dark places. The abyss is not empty, but filled with the success stories of those who have come before. The abyss is where a new world exists, but you must be in it, and then shine a light to be able to see.

Be the shining light

Your family and friends might not get it. They won’t understand why you’re trying to “ruin your career”. Instead of trying to make them understand, show them how much you want this new life. Show them  you deserve all that you desire, even if that means getting your ass kicked by entrepreneurial pursuits.

Nobody said it would be be easy, and despite your efforts to be a reclusive artist, it’s become clear you must actually be active in your business. That means interaction, that means showing people the artist within, and that means no more naiveté about systems and what works to help you build a business.

It also means you can’t be caught holding. No more ace up your sleeve—no more crutches. I unsubscribed from that email list this weekend. I will not receive another email from that group again. If those people want me so bad, they can come find me, and then maybe we can work something out on my terms.

It’s time to be the shining light in your life. It’s time to become the glowing element that creates awe and wonder in others, and the only way that happens is if you make strides to be the best creative businessperson possible. It’s time for you to be a beacon for your tribe. You are part way into the abyss now, but there are others above you. Shine for them, and show them the way.

Now is the time. Leap!



[photo credit]
Recent Posts
Showing 23 comments
  • Allison Sharpe

    This post gives me diarrhea!! Some days I literally feel like I drank cement and am frozen. Fear is evil!!! I trust this is the year to break out and I’m excited. Excited for me, and you. Can’t wait to see all you put out there Dave.

    • Dave Conrey

      You want to break out Allison? I just gave you a hammer. Now start swinging!

      Wipe your butt first.

  • cassie

    YES! YES! YES! I have been out of the 9 to 5 workforce for 1.5 years now. It’s hard to imagine going back there. I don’t hate my previous job but I love my current work more. I have not earned as much or equal to what I was on before but I know that will change in the future. Stepping outside the conventional role and working because you love to is something that all of us should strive for

  • Melanie

    Love this Dave! Sharing it!

    • Dave Conrey

      Cool, Melanie. Glad you enjoyed it.

  • Lindsay

    I’ve been out 8.5 years. NEVER going back. You nailed this. Thanks, Dave.

  • Elena

    Beautiful and poignant Dave. I made the leap 8 yrs ago.
    Both feet, delusions of my success ready, wings unfolding on the way down. Next to the birth of my son…starting my own business was the.scariest and most satisfying move of my life.

    A rockin spiritual journey.

    • Dave Conrey

      Totally agree, Elena. Scary and exhilarating.

  • Gloria

    Dave, Thank you for eloquently expressing the internal shift that happens when we finally live life on our own terms (regardless of what society believes is “success”). I made the leap 8 years ago into my own freelance graphic design biz and running a yoga studio…and have never looked back, despite temptations from head hunters. At one point, a particularly tempting full-time job presented itself. I asked myself “how much would these guys have to pay me to convince me to give up time with my family, my own creative choices, yoga classes on a Friday morning or a walk on a beautiful Tuesday afternoon?” The answer was clearly “there’s no amount”. I believe when we learn to value what success and freedom mean to us individually on a personal, energetic and soulful level, our choices become clear. It’s not always easy to be a multi-passionate entrepreneur… and I’d have it no other way!

    • Dave Conrey

      Most excellent, Gloria. Thanks for sharing your inspiring story.

  • Rachel

    Love this. Thank you for sharing this part of your journey!

    • Dave Conrey

      Thanks Rachel. I’m happy to share.

  • Kelly

    As someone who is totally struggling with this very thing RIGHT now, this post spoke to me deeply. That fear is nearly paralyzing, but I know that when I finally take the leap, I will be more free than ever. Your comments about the things you truly value in life by being in your current role are so right on, and those are what I crave most, other than fully doing what I love to do. I feel confident that I will get there in the right time, and it will be the most liberating (and maybe scary) thing I will ever do. Awesome, awesome post!

    • Dave Conrey

      Thanks, Kelly. I definitely want to clarify that I want people to make smart decision with their future careers, make a deal with yourself and stick to that plan. Once you hit that moment where you’re ready to dive in, do so with grace and fire and go after it with all you’ve got in you.

  • Dave! THANK YOU for continuing to put yourself out there and for being brave enough to remain transparent. I’m jumping both with both feet…and it’s SCARY…but you know what? I’ve never felt more alive! :-)

    • Dave Conrey

      Like diving into an ice cold pond. It’s the entry that is the toughest part. The rest is just swimming.

  • Vanja Stace

    WOW. I read the post and got goosebumps, and am feeling a bit shaky to be honest. I have been working for myself for a few months now and am appreciating the moments I spend with my family, and the fact I get to feel sunshine on my skin Monday through till Friday instead of being stuck in a shitty office with bad lighting. I too have job emails come in and I check them out. I think yeah the money would be good, regular and reliable, but I remind myself that I’m building something important here. But I feel guilty because I’m not bringing in as much $$$ as I used to, and I can see my hubby going into his daily grind not 100% happy…

    As I’m typing this my two furkids are sleeping on my desk, I have a brightly decorated office and plenty of sunshine and fresh air. I just came back from the gym and didn’t have to ask for permission. Your post has made me realise I need to keep going, keep building, so that I can keep my freedom and drag hubby over to this side. Thank you!!!

    • Dave Conrey

      Exactly, Vanja. We can’t get caught up in the quagmire of relating success to the amount of money we generate. Sure, we want to make enough to pay the bills, but if you know you’re working toward your true purpose, as long as you keep pushing forward, keep jumping, and doing the necessary work, the money will find you because people will find you. Be a voice for those who have no voice, and be a beacon for those that need a light to guide them. Eventually you will become a massively powerful force.

      You said you’re debating on B-School because of worthiness. Well, you are worthy, I can promise you that, because everyone is worthy. However, not everyone who joins will find success, and it usually comes from not taking the leap.

      On Wednesday, I’m going to be going deeper into why B-School is important and how it can help others. I’m also going to show how I’m sweetening the pot a bit. I invite you to stay tuned for that announcement.

      Thanks for swinging by.