Losing It All and Starting Over

“If I inherit a lot of money, I may feel a fiduciary obligation to preserve the corpus. But a person who creates wealth, a risk-taker, says ‘If I lose it all, I can go out and create it again.’ “ – Patrick Rooney, director of research, Center on Philanthropy , Indiana University.

It’s rare that words have such impact they manage to distract me from my never-ending blogosphere hopping. I usually read, nod (or curse) and move on. The attention span of a gnat, I know.

At mention of entrepreneurship, something inside me perks. I am, an entrepreneur, with vision upon vision buoying plan upon plan. I have milestones and paths, goals to reach.

I see the future, and I am going to make it mine. But I digress. (And I’m probably getting a little cocky for some people’s tastes.)

The quotation above is worth thinking over – and over, and over, and over. One of the most common mindsets we perceive in small business, freelancing and blogging is fear. Fear of faith. Fear of trying. Fear of failure. Fear of success. Fear of losing it all in an instant. Fear of hoping against hope. Fear of having your hopes crushed.

I don’t understand fear, I’ll admit. Fear – this type of fear – isn’t something that I care to rent space in my spirit. No vacancies, last call, out you go.

As far as I’m concerned, failure doesn’t exist. Everything I live is a learning experience. There is no failure. There is only an attempt that didn’t turn out as expected. So what does work? Where did I go wrong? How can I fix this? What other routes can I take to reach my goal?

Many people would call me a risk-taker, and maybe I am. Others call me calculating and know that there’s always a strategy to everything I do. I do take chances. I do leap with faith. I do know I might fall.

That trust in myself has let me learn that if I lose it all, I can go out and try again. This blog? This business? If it fails, I have concrete proof that I can make it at least as far as today – and I have the experience and knowledge to know how to do it better next time.

Let’s say I win the lottery. Let’s say that my ship comes in and suddenly, here’s money staring me in the face. Honestly? I’d probably blow a good chunk of it, like a starving man finally able to glut himself silly. (Don’t worry. I’d put away money for my kids and buy a house, too.)

But I wouldn’t care much about the money. I didn’t make it happen. It didn’t come from me. I didn’t build anything that gave me that wealth. I didn’t pour heart into something that could keep me, Harry and my family off the street.

Harry often says that if you teach a man to fish, you’ve given him the gift of self-sufficiency. (Or something like that. His saying is wittier than my interpretation.)

I believe that with every risk I take, I am teaching myself. I am giving myself the gift of learning how to try and how to fail so that I can try again with more wisdom. I am teaching myself about succeeding. About reaching goals. About the value of creation using your mind, your heart and your skills.

With every dollar I create from my efforts, I am proving to myself that I can earn wealth on my own. (Alright, wealth is debatable. Comfortable living is probably closer to the truth.) I’m showing myself that I can support my family, that I can be hired, that I can be of value to others.

No matter what happens to me, to Harry or to our business, we will always be able to do this again. Know what that means? It means that taking a chance is always worth the risk.

Post by James Chartrand

James Chartrand is an expert copywriter and the owner of Men with Pens and Damn Fine Words, the game-changing writing course for business owners. She loves the color blue, her kids, Nike sneakers and ice skating.

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  1. James, I think you’ve completely captured the entrepreneurial spirit here. I especially like this:

    “I see the future, and I am going to make it mine.”

    Isn’t that what it’s all about? It sure as hell is one of my ongoing mantras. Don’t wait for success, make it. Reach out and grab hold. Wrestle fortune to the ground until it submits.

    And, God forbid, disaster strikes, start all over again. But this time, do it wiser, better.

    If I had to start over as a freelancer tomorrow, I’d hit every success threshold that much quicker because I’ve screwed up enough to know what not to do.

    Bob Younce at the Writing Journey’s last blog post..Disappointed, Frustrated and Angry

  2. James,
    I couldn’t agree more if I had written it myself. My entire life has been stepping stonesof lessons that have built on top of each other. Each job, each adventure, each fork in the road that others would have called a failure has brought me right here so that I can start this next one. I have collected all of these skills in the school of life and wouldn’t have it any other way. No matter what happens, I always have the confidence of knowing that if I’m breathing, I’m not down and out.

    I can start over.

    Wendi Kelly’s last blog post..Loving Laughter

  3. Now, I know I was speaking rather loudly on my patio last night but I didn’t think people could hear me all the way up in Montreal…

    I wasn’t saying the same thing you’ve written here, James. I was speaking to the opposite, to the lack of faith in myself.

    When you are in a bad situation, it becomes so easy to allow yourself to be beaten down by what surrounds you each day. The negative feelings swirl around and cling to you (or me as it happens to be at the moment).

    And yet, I am an exuberant person by nature and it cannot hold me down for long. A post like this reminds me that I too have skillz and it’s just a matter of putting them to use. 🙂

    Great post!

    Jamie Grove – How Not To Write’s last blog post..How I Almost Started Writing: York

  4. @ Jamie – I think we all have those moments of feeling beaten down to the point that it’s hard to realize what we really can do. Damn, but don’t we make failure a real big word in our minds.

    It’s tough to change how we feel about not making it. I know this. It’s hard to see the knocks as a gift. I think doubly so for creative people – we do so love our misery.

    What’s important is to be able to see the good in every negative. Even in my worst moments, I always think to myself, “Well, something good will come of this. Don’t know what yet, but I can’t wait to see what it is.”

    @ Wendi – I was actually thinking of you a little as I wrote this post. I know you had set your fiction aside and that you recently breathed life back into it – and it liberated you, I think. That was the perfect example of knowing that you’d come that far before, you could go that far again.

    And now look? You’ve gone even further. Pretty cool, huh?

    @ Bob –

    I’d hit every success threshold that much quicker because I’ve screwed up enough to know what not to do.

    And knowing that is a damned good feeling. Who can argue with faster success, no matter what brought you to it?

  5. Brett Legree says:

    A very smart post James, and one that should also make us think, “I’m thankful that I am able to try, and try again”. We are fortunate to have the skills and resources to do this, and to live in a place where we can make it happen, even after things don’t work out quite as intended.

    I like that.

    There really is no failure, only learning, and opportunity. You might fall, but you’ll get back up again.

    Brett Legree’s last blog post..draw your own line.

  6. James, I can’t agree more with this post! I’ve actually seen this happen — an acquaintance of mine has experienced earning wealth and having it snatched away. As a child, he lived in the slums of Puerto Rico, scraping around for food. After fighting in one of our wars, he moved to the Midwest and somehow made a fortune. It seems as though he invented his own niche with odd jobs and went for it.

    He ended up marrying a spoiled brat and wouldn’t you know, it didn’t work out. He basically left the house with just his toothbrush, telling his soon-to-be ex-wife that she would need his riches, b/c she wasn’t clever enough to make her own and would likely starve to death without his help.

    So, what did he do? He went back into the world and made more than what he lost. He knew that he could survive poverty (if it would come to that), but that he could also work his way out of it. He ended up retiring way earlier than normal and now lives off the riches he made the second time. The entrepreneurial attitude pulled him through.

    Now, I don’t have any experience with entrepreneurship, so I try to keep this story in mind. I hope to be able to gain the confidence and know-how to get myself on the right path 🙂

    r.l.david02 – TKD Happiness’s last blog post..Why can’t I gain belt rank? (part 1)

  7. This is an awesome post, James. We all feel a bit in the dumps sometimes and pulling yourself out and mustering on truly makes you successful. I, too, try to see everything as a learning experience. Every shitty thing that has ever happened to me has taught me something or prepared me for something coming in my life.

    Hindsight might be 20/20 but if you can look at things in front of you with some wisdom and understand that it’s all about the journey instead of the destination, you’ll sleep better at night instead of just waiting for life to get better.

    Dana’s last blog post..Writers: Be Your Own Publicist

  8. Jamie Simmerman says:

    You know, my dad recently left me a chunk of money that we didn’t even know he had. Suddenly, I could buy whatever I wanted at the grocery store, take my kids to a movie, eat somewhere other than McDonald’s, and smile at the mailbox everyday.

    But you know, I didn’t stop writing. I’ve worked too hard to get this far. It’s who I am now. I discovered I still love to write. (After I had the freedom to turn down crap jobs writing about insurance and security cameras.)

    And you’re right, that money is different than money that I earn myself. Funny how that makes a differnece.

    Nice post, James. It makes one think deep.

  9. James,

    Great post as always and once again, you’re struck the nerve which I find exposed in my own life.

    I’m getting ready to pursue a new venture. I’ve done this before and been successful. However, this time, with this venture, I’m spending WAY too much time trying to dot all the i’s and cross all the t’s. I’m so focused on “doing it correctly” that I’m not doing it!!!!

    I wouldn’t have called it FEAR until I read your post. THANKS!!!!

    Virtual Impax’s last blog post..Increasing Blog Traffic: Trolls and Drive By Readers

  10. Well-written!

    I definitely agree that everything is a learning experience. The difference between success and failure is often determined by whether or not you pick yourself up and go on.

    Laura Spencer’s last blog post..Of Note: Words of Redemption

  11. 100% True.

    This is why self-made people find it easier to bounce back after a tremendous “failure.”

    You can lose the money in a flash, but you haven’t lost the skills that got it for you in the first place 🙂

    Dave Navarro’s last blog post..Would The World Stop If You Did?

  12. @ Dave – I think many people tend to forget that so easily. All they feel is loss or the sense they missed the high jump. You’re so right – no one loses acquired skills.

    @ Laura – The problem is that many people just don’t know how to pick themselves up and go on. We each have our weaknesses and learning how to cope with them is the tough one.

    @ Virtual – Damned straight it’s fear. The funny thing is, that didn’t hit me until I started writing. We fear failure so much that we forget the successes we’re earning. Now go do whatever you’ve been procrastinating on 😉

    @ Jamie – The differences in monies was clear to me a couple of weeks ago when a friend asked, “How do you feel when someone praises your website content?”

    “Well… I’m like, thanks, but I really didn’t do anything special. It just… happens.”

    “Now how do you feel when someone praises your management skills,” she asked.

    “Oh man. That, I love. I work *so* hard to be a good manager.”

    And therein lies the difference. Sometimes what is given to us without effort doesn’t carry the same meaning.

    @ Dana – Hindsight is great – but we all need to learn how to take hindsight and make it foresight. Tough stuff, that!

    @ RLD – Oh man. Now *that* takes courage. I applaud that man for knowing so deeply he can do it again, especially considering where he came from.

    @ Brett – We’re all going to start quoting Yoda again, aren’t we…

  13. The picture James, that picture…and your headline…no fair…

    one step forward and then one more and then one more….with Puck and Merlin behind the scenes…

    You made me cry again, but sweet tears this time of, “he gets it.”…

    Janice C Cartier’s last blog post..A Goal Setting Template- Part 4

  14. @ Janice – I do get it, ma belle. I always did, even though I’m a stubborn bastard about it at times 🙂

  15. John Hoff - eVentureBiz says:

    I wrote on article a while back where I talked about what you need to remember when it comes to failing is not the fact that you failed – what you need to “remember” was the successful attempt.

    John Hoff – eVentureBiz’s last blog post..Real Estate Challenge: Which Is A Better Investment – Owning or Renting and Saving

  16. James,

    I just posted about this yesterday. I agree completely; not that failure is great, but that there’s a lot of good hiding in the dross if you’re ready to learn.

    No regrets for me. I wouldn’t be who I am without every. single. moment.

    If you haven’t had any bitter, you don’t know when you’re tasting sweet.



    Kelly’s last blog post..6 Signs That Mean Your Business Is Going to Have to Try Harder

  17. Brett Legree says:


    For a short little wrinkled old man with green skin and hair coming out of his ears, Yoda’s a pretty smart guy…


    Very true – how can you know what light is, if you’ve never seen the dark.

    Brett Legree’s last blog post..draw your own line.

  18. I find the rewards have been sweetest when I find myslef feeling apprehension about something big I am preparing to take on. More than anything I fear being held captive by fear – and never attempting anything worthwhile. When I hear whispers of self-doubt, I just close my eyes, (say a prayer) and jump in. Sink or swim.

    Kimberly Ben’s last blog post..When You Need a Little Help

  19. She smiles . Damn, Quebecois. The artist grabs her feelings off her sleeves, rolls up those same shirt sleeves and heads back to work… one step, another…then a leap….;-)

    Janice C Cartier’s last blog post..A Goal Setting Template- Part 4

  20. It seems you have a very advanced soul, James.
    When our souls evolve to certain point, physical limitations don’t threaten us so much — in other words, we don’t see them as threats as others do.
    Very interesting. Thank you for sharing.

    Akemi – Yes to Me’s last blog post..Real Life Lessons On How To Become A Successful Entrepreneur

  21. Michael Martine says:

    I know people who keep make tons of money, lose it, then make it all back (this is continuous, which means they have other problems, LOL). We’re indoctrinated that making money is supposed to be arduous and difficult. It’s not hard at all. It certainly can be a lot of work, but one of the biggest surprises of my life has been realizing how easy it can be (although I am far from wealthy).

    There is a fantastic saying I heard once upon a time: the obstacle is the path.

    Michael Martine’s last blog post..What Conversion Is, Why it Matters, and How to Improve It

  22. The trick is not having money, the trick is knowing how to make money. If money came to you easily–you inherit money or you win the lottery, etc.,– but you don’t know how to take care of money, you’ll lose it. If you start out with nothing in life but along the way learn how to make and take care of money, you’ll become wealthy; you can also remake the money if you lose it. Being wealthy is a state of mind.

    Marelisa’s last blog post..How to Become a Renaissance Man/Woman

  23. @ Marelisa – No, the trick is not caring about the money, I think 🙂 Like you said, a state of mind.

    @ Michael – Okay, dammit. My path is full of stones!! Where are those gladiators! My chariot is stuck!

    @ Akemi – Bless you. Though I think people here would be quick to tell you my soul is still six years old 😉

    @ Janice РMaudit Qu̩becois, ma belle. Never damn us. Our road to hell is already paved.

    @ Kimberly – I like that. That feeling of tingling… and then… yeah, you do it. What a feeling when you come out alive on the other end, eh?

    @ Kelly – I must’ve eaten a lot of bitter, because these days, everything tastes sweet.

    @ John – Ah, John. You of all people know my memory is shot.

    James Chartrand – Men with Pens’s last blog post..Losing It All and Starting Over

  24. Aughhh James. Damn is short for “Hell fire and damnation! ” where I come from….it’s more a curse at me than a damning of you, and used for emphasis. It’s one of the few “curses” I allow myself… but okay, mon cher.

    Chariots? That’s when you need a helicopter… 🙂

    Janice C Cartier’s last blog post..A Goal Setting Template- Part 4

  25. Great thoughts, James. Sometimes, freelancers have to push the boundaries of their comfort zones to succeed.

    And on the subject of failure, I particularly enjoy this quotation from Thomas Edison: “I have not failed. I have just found ten thousand ways that won’t work.”

    Debbi’s last blog post..Lessons Learned (Part 3): Diversify, But Know Your Limitations

  26. Hi James – I almost missed this wonderful post. Lillie mentioned it on her blog and I was thinking – how the hell did I miss that.

    It’s a wonderful quote and I love the way you’ve explained it. I guess a lot of folk would take the cash, but it’s far better to have that tool to create it to begin with.

    I think the greatest feeling from buying stuff doesn’t come from the stuff, it comes from the satisfaction you get, knowing it was your hard work that helped you do it.

    I’ve never won the lottery, but it’s hard to imagine getting the same satisfaction from that.

    Cath Lawson’s last blog post..Are You Ready To Give Up The Day Job?

  27. Funny but is my husband’s pov too. I am a little less so despite having been there and back. Surviving and thriving has not made me less fearful (though I don’t life the term because it doesn’t quite capture the reality). A little fear is grounding.

  28. @ Annie Perhaps, instead of fear (if you don’t like the term), you could think of your hesitation as judgment. There’s a big difference between calculated risk-taking and foolhardiness. Fools rush in and all that.

    Debbi’s last blog post..Web Revolution for Writers of All Stripes

  29. Stan Lifts says:

    There are many people right now that in these tough economic times feel like they have lost it all. If only people could focus on the things that they DO have they would be so much better off. I like your point of view.. it was well thought out.
    .-= Stan Lifts´s last blog ..Lift and Tilt Table =-.

  30. @ Stan – I really like this post. Thanks for commenting, because you gave me the opportunity to revisit it.

    People *always* have something. Health. Love. Friendship. Hope. There is never a state of being where a person has nothing at all, unless they’re dead.

    I think our society has become to negative-thought minded, and people focus on their fears and worries, paralyzing themselves. Maybe a few more posts like this one from more people would help them realize that fear-focusing gets no one anywhere.

  31. I agree. We all hove so much to be thankful for. It gets lost in all the things we need or want or wish we could have. I guess the very thing that drives us to succeed in life is the very thing that can make us the most unhappy. Yearning for something better is a blessing and a curse!

    .-= Jeff Hamis´s last blog ..Tilt Table Bellows =-.

  32. Bounce back – is the best response I had from someone in a bad situation. Bounce back and do better.

  33. Stuart Williams says:

    It is sometimes hard to wake up in the morning after you lost everything. In 2003, I lost my wife and child due to PreEclampsia. Then a came into a large court settlement and got caught up in the Real Estate boom and played the stock market. I lost all of that too.

    My current wife and I picked ourselves up and are on the way back. It is painfully slow, still have a lot of debt, IRS, etc. But what does it matter? Money is created out of thin air and really doesn’t exist if you think about it. If someday it is printed to worthlessness, who cares what you bank account is?

    Just remember that in 100 years, you will not care what your financial worth was. The sun will rise, you won’t be there and all that you worry about today will be of no consequence.


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