Snowy Road

We’ve done our­selves a dis­ser­vice in the way we’ve come to define suc­cess and failure.

Suc­cess = Try­ing and get­ting the result you hoped for

Fail­ure = Try­ing and get­ting some result short of the one hoped for

Thomas Edi­son said some­thing really pow­er­ful in this quote. We miss it these days because we’ve heard it so much, but it’s real.

I haven’t failed. I’ve just found 10,000 ways it won’t work.” - Thomas Edison

I’m one of those weirdos who’s grown up with the desire to be suc­cess­ful. We’re a hard group to find. We tend to wear pants or shorts, dresses or skirts. We tend to drive cars or walk, run, ride a bike or the bus, maybe the train. We usu­ally have a job or own a busi­ness or per­haps no job. We try stuff. Each try is an oppor­tu­nity to suc­ceed or fail and we loathe the fail option. It messes with our heads. We think lim­it­ing thoughts:

Should I have tried in the first place?”

Why was I so fool­ish as to think I could have pulled that off. I knew nothing.”

I’m embar­rassed.”

I’ve got to make up for that fail­ure before I dare try again…assuming I should dare again at all.”

Life’s not very long. 80–100 years max. There’s a lot to do; there’s a lot to expe­ri­ence. Let’s not go gen­tle into that good night.


At 20, a friend and I dared buy a condo in Boul­der, CO. Boy was that the wrong time to dare. It wasn’t a win. The two own­ers before us dared and won. In 6 total years they expe­ri­enced a com­bined $100,000 in appre­ci­a­tion. in 10 years of own­ing we made did­dly. I car­ried the weight of that non-success for some time. How could I have thought that a good idea? What did I know about home buy­ing at 20? I didn’t know squat about what could go wrong. I’d never seen a down­turn in the real estate mar­ket. That’s why 20 year olds have no busi­ness try­ing that. So dumb. Stay rea­son­able and make sure that doesn’t hap­pen again.

That’s what we do!!! Can you believe that? I can’t believe it. I dared. I lost. I knew so much more than before I started. I advised friends when their day came to buy a home. I was actu­ally closer to suc­cess than before I started because I gained expe­ri­ence. Unfor­tu­nately, I was turn­ing that expe­ri­ence into a stop sign. That’s not expe­ri­ence. That’s not wis­dom. That’s not liv­ing. That’s not suc­cess. That…is failure.



Let’s change how we iden­tify success:

Suc­cess = Trying

Fail­ure = Being a badass who’s try­ing stuff

Sara Blakely is the founder of Spanx, which has done pretty well as an orga­ni­za­tion. You may have heard of it. In turn, she’s done pretty well for her­self accord­ing to Forbes, as the youngest self-made female bil­lion­aire in the his­tory of planet Earth. In telling of her child­hood to Busi­ness Insider, she explained how her dad would ask at din­ner what she and her brother failed at that day. When they had an answer, a high-five was in order, because try­ing and suc­ceed­ing and try­ing and fail­ing are both really really pow­er­ful. Both are success.


The Fail Project

I wanted to really rede­fine suc­cess and fail­ure in my life. The year I turned 30 I decided to cre­ate a lit­tle fail project for myself (I’m 32 now):

Objec­tive: Rede­fine fail­ure. Become immune to the neg­a­tive feel­ing asso­ci­ated with fail­ure. Develop and rein­force the pos­i­tive feel­ing of being a badass who tried something.

How: Take inven­tory of life time assets, finan­cial assets, future goals, and unat­tempted past goals. Cre­ate a 1-year sched­ule of highly likely to fail tasks. Some large. Some tiny. Some that’d been on the to-do list for a long time. Some that just ran­domly came up.

Spoiler: The result wasn’t actu­ally what I expected. Immu­nity wasn’t achieved because I actu­ally suc­ceeded at a lot of stuff. I found that things I put in the “unlikely to suc­ceed at” cat­e­gory actu­ally belonged in the “rea­son­ably likely to suc­ceed at” cat­e­gory. The beau­ti­ful thing is I did come to find great pride and joy in try­ing. I came to feel the feel­ing of suc­cess from try­ing, regard­less of outcome.

This is a blog about try­ing. About risk. About tak­ing on uncer­tainty. Learn­ing. Skill devel­op­ment. About free­dom; free­dom to explore and do and go and to stop. It’s about start­ing. Show­ing up every­day. It’s about steps, small chunks, big chunks, bite-sized pieces. Plans. It’s about redefin­ing met­rics. It’s about inten­tion­al­ity. Cre­at­ing life. Beauty. Joy. Doing. Going. Regroup­ing. It’s about fail­ure. It’s about suc­cess. It’s about life being lived.

I’ve never really had a blog before. Lets give it a try.
  • slaflora

    love love love.….cheers to a start!

    • Ryan Holde­man

      Thanks! Here we go.…