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@joshsimmons | philosophy, psychology, technology
co-founder @beawimp | community manager, programming @oreillymedia
Fail Well
How to Fail & Recover Like a Pro
with i@joshsimmons.com
"If you're going to fail,
please fail loudly and sing
it as if your life depended
on it.” - Lee Yopp
Hello, world!
How to Fail
10. Lose Touch with People
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise People
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise a Client
4. Give It Away for Free
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise a Client
4. Give It Away for Free
3. Over Commit
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise a Client
4. Give It Away for Free
3. Over Commit
2. Work Without a Contract
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise a Client
4. Give It Away for Free
3. Over Commit
2. Work Without a Contract
1. Fail to Measure
10. Lose Touch with Your Clients
9. Put All Your Eggs in One Basket
8. Work Yourself Out of a Job
7. Be an Island
6. Do Everything
5. Surprise a Client
4. Give It Away for Free
3. Over Commit
2. Work Without a Contract
1. Fail to Measure
Fail Well
Managing the Relationship
Saving the Relationship
Terminating the Relationship
Managing Yourself
Manage Your Reputation
fail fast
fail often
fail well
@joshsimmons aka bluesomewhere
community strategist
open source web developer
slide deck and credits:
slideshare.net/joshsimmons/fail-well

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Fail Well

  • 1. @joshsimmons | philosophy, psychology, technology co-founder @beawimp | community manager, programming @oreillymedia Fail Well How to Fail & Recover Like a Pro with i@joshsimmons.com
  • 2. "If you're going to fail, please fail loudly and sing it as if your life depended on it.” - Lee Yopp
  • 5. 10. Lose Touch with People 10. Lose Touch with Your Clients
  • 6. 9. Put All Your Eggs in One Basket 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket
  • 7. 8. Work Yourself Out of a Job 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job
  • 8. 7. Be an Island 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island
  • 9. 6. Do Everything 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything
  • 10. 5. Surprise People 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything 5. Surprise a Client
  • 11. 4. Give It Away for Free 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything 5. Surprise a Client 4. Give It Away for Free
  • 12. 3. Over Commit 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything 5. Surprise a Client 4. Give It Away for Free 3. Over Commit
  • 13. 2. Work Without a Contract 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything 5. Surprise a Client 4. Give It Away for Free 3. Over Commit 2. Work Without a Contract
  • 14. 1. Fail to Measure 10. Lose Touch with Your Clients 9. Put All Your Eggs in One Basket 8. Work Yourself Out of a Job 7. Be an Island 6. Do Everything 5. Surprise a Client 4. Give It Away for Free 3. Over Commit 2. Work Without a Contract 1. Fail to Measure
  • 21. fail fast fail often fail well @joshsimmons aka bluesomewhere community strategist open source web developer slide deck and credits: slideshare.net/joshsimmons/fail-well

Editor's Notes

  1. I’m a community organizer and web developer, currently working on open source and web tech for O’Reilly Media. I’ve failed a LOT and in more ways than you can imagine in my career, as a freelancer, as a startup CEO, and as an employee. My goal is to help you fail well – like gymnasts who learn how to fall so they don’t injure themselves.
  2. We’re all fans of open source here, so I don’t think I need to convince you of the value of sharing. Sharing about failure is hard, but it’s important. My goal with this talk is to help you (1) learn about types of failure so you can see them coming, or at least do a better post mortem, (2) learn how to recover from failure, because failure is hard, and (3) get more comfortable talking about failure. OK, so a brief outline before we dive in: We’ll start with 10 types of failure, my top ten things NOT to do, followed by a discussion of how to recover – because we all know failures large and small are inevitable. Two notes: Sometimes I talk too fast – if I’m going too fast, raise your hand and I’ll slow down :-) Please hold questions till the end – I’ll be happy to chat in the hallway if we run out of time. Ready?
  3. This is me getting myself in over my head, a total newb taking on a level 4 white water rapid in an inflatable kayak. White water rafting is dangerous. It’s VERY likely you will fall into the river sooner or later, but there are things you can do to, well, avoid dying. First, get out from under the boat and away from other rafters! You don’t want to get trapped or slam into each other. In order to keep from drowning Look out for “strainers,” which are bushes and dead trees that you can snare you. If you get snared, climb OVER it. And don’t flip vertically, spin horizontally, otherwise your feet may get caught in the rocks on the river bed. In order to avoid bone breakage Go legs first, not head first! That’s self explanatory. Keep your legs up, so your butt absorbs the impacts from boulders – not your spine. And take a BIG breath whenever you can! You don’t know when your next breath will be. So what? The point of this illustration is to illustrate that falling out of the raft, or failure, doesn’t usually kill people – and there are things we can do to improve our odds… and though I don’t think the analogy stretches this far, failure can make us even stronger. These lessons are drawn from my experience, so the stories I tell will be in context of freelancing, agency work, and startups. But these are universal lessons... And lastly to be clear, I did not fail well. I failed badly. Please, do better than I did!
  4. How to Fail fail to measure work without a contract overcommit give it away for free surprise a client do everything be an island work yourself out of a job put all your eggs in one basket lose touch with your clients
  5. 10. Lose Touch with People Stay top of mind with your clients, coworkers, and your communities – both past and present. Most jobs are NOT advertised, so your network is your #1 resource for finding work (and staying sharp). And, in context of contract work, the shortest path to money is through the clients you already have. Attend events Send relevant news Holidays Newsletter? Blog! Maintenance contracts
  6. 9. Put All Your Eggs in One Basket Use multiple marketing channels Diversify your skills and know how to pitch yourself several different ways Have many clients, you should be able to lose a client or two without falling into a financial tailspin Or, have ins at many different companies
  7. 8. Work Yourself Out of a Job As a freelancer, you are ALWAYS looking for work to fill your project pipeline, otherwise you’ll finish a project and go pale with horror as you realize you don’t know where the next check is coming from. If you’re familiar with the concept of a sales funnel and sales cycles, well, study up! As an employee, it’s tempting to become “indispensable” so you have job security. But the reality is that you MUST be dispensable in order to get a promotion. For employees, working yourself out of a job mostly means staying sharp.
  8. 7. Be an Island Participate in communities online and off (you’re here so you’re already doing great) This is the best way to find work and stay sharp. Harking back to “Don’t Put All Your Eggs in One Basket,” consider joining multiple communities... Don’t limit yourself to the Python watering hole, join the larger engineering community.
  9. 6. Do Everything niche virtual asst biz model ad hoc team join + start a community
  10. 5. Surprise People phase or agile expectations! good/delight scope creep - amend or defer
  11. 4. Give It Away for Free always list full rate ask for referral, testimonial rec $200/hr starting!!! barter
  12. 3. Over Commit say no priorities connect / delegate / subcontract
  13. 2. Work Without a Contract not punitive short and sweet even an invoice or emails count key clauses licensing contact info & expectations payment warranty / SLA -- for apps and maintenance contract arbitration (arbitration association plz!) - nobody wants to go to court. that sucks, trust me. expiry ( friendly/plain English (ish)
  14. 1. Fail to Measure budget estimates limits / capacity growth / goals / profit
  15. FAIL WELL really, it’s about grace under fire saving the relationship terminating the relationship managing yourself managing your reputation
  16. social capital a good apology thanks amends? continue? adjust? move on?
  17. legal process make it amicable verbalize why - narrative ? refer to someone else if the client isn’t a bad client
  18. it’s not the end one step at a time empower yourself - don’t let cleaning become a displace activity (procrastinate), but it can help you regain sense of control don’t withdraw don’t lash out guilt/blame #1 comm #2 prod non-work identity
  19. don’t let it snowball be honest, be vulnerable actions speak louder than words … but having a narrative helps what do you stand for? take the high road no excuses, not even reasons - unless people ask share your lessons
  20. Thank you! Find me on Twitter and my slides on Slideshare… where I’ll be uploaded updated slides when I get to my hotel because the university wifi has Slideshare blocked  With that, go out and fail well! (Questions?)