TVC082 Life After Awesome Chris Lochhead

TVC082 Life After Awesome With Chris Lochhead

What To Do Next When You’ve ‘Made It’

This weeks show is with special guest and entrepreneurial guru, Chris Lochhead, co-author of Play Bigger and also the master behind the Legends and Losers podcast

Chris calls himself a small E-entrepreneur – with the reality of his experience being quite the opposite as true influencer. 

Staring his first company at 18, after getting thrown out of school – Chris ultimately became the head of marketing for three publicly traded technology companies in Silicon Valley. Born and raised  in Canada he moved to Silicon Valley about 21 years ago.

The last company Chris was with as head of marketing, was a company called Mercury Interactive and they sold the company for about 5 billion dollars to Hewlett Packard. After that, Chris retired for the first real time, and then ended doing coaching and consulting for start ups and venture capital firms – which lead him to started a business with two friends, called Play Bigger.

Between the independent advising and the work we did at Play Bigger, the three of us and another genius named Kevin Maney, wrote this book called Play Bigger. We broke down this discipline called category design in the book, which came out in June of 2016, and then I retired – officially.  

With all that behind him, and no stranger to being the top of the corporate and innovation food chain – Chris made a conscious decision on what was next. Spending a lot of time with my family in beautiful Santa Cruz, California.  Now, Chris is “mostly retired” and his passion in life is his show the Legends and Losers podcast. Well worth having on your Must Listen To list.


…so when there’s waves I surf. I surfed this morning. I still do a little bit of speaking and I still do a very little bit of work with a few companies.  Mostly, I’m just trying to be half the man my mother thinks I am, or mother thinks I should be. Something like that.


What does life after awesome look like?

How does someone who has made their career happen, invested time and IP into companies, being part of many mergers and acquisitions – move on to What’s Next?

By the way, before we go into this it’s very important to realise that many times what is defined as AWESOME is usually just what we feel we need, should and must be doing based on our own expectations or what is ingrained in us as we grow up. This expectation builds up.

Many of us chase titles and a place in society connected to getting a role, working through the ranks and having your businesses define who you are – without even realising it. A kind of success conditioning. Along the way there is often collateral damage as personal and commercial life became out of balance. 

So the big issue question is what happens to those high achievers once they have ticked all those boxes how do you  stay relevant and decide what to do next.

Chris: It’s such a powerful question. You never see anything or hear anything, really, in the world about what happens after you win. Right? It’s all about winning. It’s all about getting to whatever this place is and then if you get to whatever your definition of that place is, then what the F?

We don’t talk about that. Here’s the thing, in a lot of ways life as you know, is about how we identify with ourselves and who we are for us.  I think a challenge for a lot of entrepreneurs, a lot of senior executive is how you define yourself.

  • Who you are, for yourself.
  • If who you are is I’m a CEO or I’m a CMO or I’m a UFO or whatever you think you are, how are you in all aspects of life?

I identify deeply as I did almost nothing else or very little other things in my life from age 18 to 38, so I understand how that happens.  I think it’s about building and designing a life and therefore, an exactly, and therefore your identity and experience of yourself.

That’s broad. It’s big and it’s scary for many people. 

What to Do When You Need To Discover Life After ‘Awesome’

Here are 5  key tips to help you get grounded in the chaos when your title is no longer the thing that lights you up:

  1. Look around the box
  2. You can’t rise without a fall
  3. Be the captain of your ship
  4. Redefine Awesome
  5. Evolve

1. The Ability To See Around The Box – Not Just Outside Of It

Your ability to see outside the box and look around the corners is something you might take for granted, but a lot of people just sit on the inside the rank, and they are on the treadmill. They didn’t even think to peak around the sides until it was not an option.

We don’t teach people how to look around the corners. We teach people to go to uni, and we teach people to think and apply for jobs, and get the mortgage, and the house, and the bigger car, and the three kids, and the dog, and boom, boom, boom, and then you can get stuck on the treadmill. For many  leaders when you talk about defining yourself – most people don’t even think about those words until they’re had a major breakdown or something side swiped them and they are forced to reflect. 

Staying Agile In Your Moment Of Truth

It’s very easy for us to be lulled to sleep.  Some people stand up when a major change happens and that defines them, and some people crumble, and that defines them.

There are these moments of truth.

What is it that people do in those moments and how we collectively over a lifetime make the choices to be who we become, or to not become who we could become. 

For example, Chris tells this example of Will Little a guest on Legends and Losers: 

Will Little lives in Philadelphia. He grew up on the streets of Philadelphia and ended up in a gang. Will has been convicted of murder three and he served 10 years for that.

Will is one of the most intelligent, deeply committed, and inspiring, talented human beings you’re ever going to meet. What Will shared with me is when he was in prison, a place that for the most part makes criminals better at being criminals

Chris asked Will about that and he said that is what happens in prison, so it’s not just a myth, but more importantly, he made a decision that he grew up without a father in a really terrible way, and that wasn’t okay. His girlfriend at the time was pregnant when he went into prison for murder and he said, “I am not going to do that to my son.”

  • He made a decision in prison, to become a man and to educate himself and it’s an incredibly powerful story.

We all have these moments in our lives, and in those moments of truth we make a decision about who we’re going to be and we design our life in those moments.

Those moments of truth. Those moments for people that make them, and those moments that break them.

2. You Can’t Rise Without The Odd Fall – Be Brave

There’s not such thing as a legend who’s not a loser. It’s incredible.

Will Little – A barber today,  and the thing that he loves to do the most is public speak. He’s a poet. He live performs his poems and he gives these insane motivational speeches. To call him a motivational speaker does not to justice to what happens. When he’s in the room, he radiates. On one hand, of course, he’s defined by his past, but what he has done with that defines who he is in life now.  Someone who wants to teach peace, to redefine choices versus chance.

  • Will transformed himself and now he lives every day of his life with a commitment to do as much good in the world as he can.

That decision, that loser to legend decision that makes us or breaks us decision, whether it’s as dramatic as Will’s situation, or much less dramatic like maybe yours or mine, but for all of us it seems dramatic at the time.

We all have our moments that we can come back from. Stronger, wiser, kinder and with a better perspective. It is a choice. It does not mean throwing out financial prosperity, being the top of your business, building an empire as  goals – it means considering the journey as you achieve it. 


3. You are the captain of your ship – set a new direction as the landscape changes

We’re all leaders in life. It does not matter what defines you is what you do with your day. We have the same number of minutes in the day as Richard Branson, as Beyonce, as Chris Lochhead, as Will Little, as myself.When you get up in the morning, you have a decision every day. What are you going to do with that time? 

Tomorrow is promised to no one.

You don’t need chaos to make a decision and to design your life.  On a daily basis create lasting habits where your daily activities create a ripple effect so you’re not waiting for one big thing to create momentum for life that you love. You’re actually leading now.

If you get stuck remember two things:

a) Is this a knowing what to do problem? Do I not know what to do – if not then I need to get some help, advice or search for info)

b) Is a doing it problem? Do I know what to do and I’m just not doing it? 


4. Redefining Awesome – Your Power

Be conscious. Make your decision now and plan. Don’t just think that everything’s going to unfold. You need to be in charge.

You need to be curious. People’s fear of the unknown prevents them from looking around the box. Fulfilment and happiness are just as important on a daily basis as big milestones. What is Awesome?

Qualifications or character. Where do you want to grow. How can you evolve both?

When you get the big title, that’s great. You get that thing called positional power. For example: Chief Marketing Officer of a billion dollar software company.

  1. Have a budget. I have a signing authority.
  2. Can hire and fire people
  3. There is truly positional power.

The best is when that is combined with The most powerful power.  Who you are. Not just your title:

  1. How you interact with other people
  2. How you treat other people
  3. The quality of your ideas
  4. Leading By Example  – do you execute the way you say you’re going to execute
  5. Do you understand the difference between results and no results plus an excuse
  6. Are you someone that can be counted on in the foxhole
  7. Are you someone who is committed to being smart
  8. Are you someone who’s committed to getting to the outcome or the answer as opposed to you being personally right? 

The kind of a person with or without positional power has the most power, because they’re present and they earn whatever acceptance for their ideas or behaviours or information. If they’re building something.

Whatever it is, they’re accepted by the group because of who they are as opposed to positional power that they have.

5. Evolve For Life After ‘Awesome’

Blending your qualifications and your character at once, and growing. There are always options. Ways to use your experience, to mentor, to create new ideas and opportunities or to  redefine what your ideal week looks like. 

We’re continuing evolving. Life isn’t about performing as well as being present and purposeful.

It’s the combination of results and character.  You literally will have no more time than you do right now.  Get Off Autopilot

We encourage you to carve out your space people. To ask your questions not to  be ruled by What Now – But instead ask What If and Why not?

  • Who are you?
  • What do you create?
  • What’s your secret source?
  • What do you love the most?

Bring that into your job, communicate with people you work with, spend some time with your kids, put the iPad down, go do something fun again you never had time for. Whatever it is. This is the time you have to create the life that you love now. Don’t wait for someone to come and give you a magic wand.

Life after awesome means you start what you’re working on right now.

Are you doing the work and keep learning. 

This is really a message for people who do things with life. If you’re serially buying books, downloading podcast, going to conferences and nothing is changing, it’s probably because you’re not doing the work. The one thing that separates those who are truly successful from the ones that are the dreamers, are the hard work bits in between. The ability to look up, be curious, be agile, ask questions and keep learning.

The real reward is the journey. That’s the big aha. The reward is we get to have a life and a career or business of our design. That’s the reward.

Be brave, there is never a dead end, just peak around the corner or create a fork in the road that wasn’t there before.

There is always life after “awesome” as we can constantly evolve what awesome looks like.

Giving back and getting recognition also means creating space for yourself to figure out what’s important. What do you value the most now.  


Please reach out if you feel you’ve hit the wall in terms of career, things weren’t as you expected all the rose tinted glasses of all those years of hard work have suddenly dimmed. We are here to help, answer questions and create a roadmap for a remarkable what’s next. 

I hope you enjoyed this entertaining and authentic episode with Chris.  Thank you for tuning into The Vitality Coach podcast – helping you be the CEO of your business and your life. Remember, you will never have more time than you do right now, so use it wisely.

Choose those you hang out with, love what you do, and be conscious and present. It’s an incredible life. Happy day to you all listening.

Stay healthy, wealthy and wise.


Yours in Vitality





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