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8 Y E A R S I N T H E G A M E
L E A R N F R O M M Y M I S TA K E S :
W E L C O M E T O T H E
L A S T 8 Y E A R S O F M Y
P R O F E S S I O N A L L I F E .
H I , I ’ M I A N .
B U I L D C R E ...
I N T H E B E G I N N I N G …
• 1998 - I love PaintShop Pro and Flash, but I can’t understand these weird smudges
that app...
H O W T O C L I M B T H E L A D D E R
• Bullshit your way into a job where you have to code way above your skill
level, in...
O R AT L E A S T T H AT ’ S
H O W I D I D I T.
B U T L E T S G E T D O W N T O B U S I N E S S
W H Y I S TA R T E D M Y O W N B U S I N E S S
• Opportunity. As the business I was working for imploded,
clients who knew...
IS TO DO IT.
T H E O N LY WAY T O D O I T,
SO I DID, AND HERE I AM. 

NOW LETS TALK ABOUT WHAT I’VE
LEARNED.
HIRING.
L E S S O N # 1
– M E , 

I F Y O U S E N D M E A R E S U M E W I T H O U T A C O V E R L E T T E R .
“…”
T H E PA I N F U L T R U T H
• One night, at about 3am, you’re going to realize that
you need help.
• You’re going to look...
P R O S A N D C O N S O F C O N T R A C T O R S
• Pro - Easy to have them work here and there to help you manage
your band...
P R O S A N D C O N S O F E M P L O Y E E S
• Pro - You have much more control over their availability.
• Con - In order t...
• Specialization is for insects. 

Job responsibilities change all the time in a small business, you need people
who aren’...
CLIENTS.
L E S S O N # 2
– M E
“Don’t do nobody no favors.”
LEARNING TO MANAGE CLIENTS IS ONE OF
THE HARDEST LESSONS YOU WILL LEARN,
BUT IT BOILS DOWN TO ONE VERY
IMPORTANT SKILL.
SAYING “NO”.
• You, and only you, teach people how to treat you.

People will insult you, walk all over you, and generally treat you li...
PROJECTS.
L E S S O N # 3
– A L S O M E
“This project sucks.”
EVERY PROJECT IS AN OPPORTUNITY TO IMPROVE,
BECOME MORE PROFITABLE, AND GROW YOUR
BUSINESS.
!
THIS IS WHERE YOU TURN CUSTO...
• You, and only you, control the project scope.

Scope creep. It is the stuff of nightmares. Suddenly your simple project ...
L E S S O N # 4
YOUR TEAM.
– S T I L L M E
“Is it done yet?”
WHETHER IT’S YOUR OWN TEAM OR YOU’RE
CONTRACTING FOR SOMEONE ELSE, THESE ARE
RELATIONSHIPS THAT CAN MAKE OR BREAK YOU.
!
P...
• Why can’t everyone just get along?

Designers and developers tend to have very different, and sometimes opposing persona...
GROWTH.
L E S S O N # 5
– M E
“Growth is terrifying.”
GROWTH, AND SUSTAINING IT, IS HARD. WITH
STRATEGY AND PLANNING, YOU CAN HAVE YOUR CAKE
AND EAT IT TOO.
!
YOU ARE IN THE DR...
• Planning is everything.

Do you know how you’re going to handle growth? I think we have a tendency to plan for the worst...
ARE YOU READY?
# T H E F I N A L L E S S O N
– I L L I D A N S T O R M R A G E , D E M O N H U N T E R
“You are not prepared.”
WHETHER YOU’RE READY TO STRIKE OUT ON YOUR
OWN IS A VERY PERSONAL DECISION, BUT HERE ARE A
FEW QUESTIONS TO HELP GAUGE YOU...
• Are you confident?

If you aren’t confident in yourself, what you’re charging, and know in your bones that your work
is ...
QUESTIONS?
hit me up on twitter @wilsonography
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Learn From My Mistakes - 8 Years in the Life | WordCamp GR 2014

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Looking to start your own design/dev business? Learn from my mistakes! After pondering my misadventures I've compiled this talk to give you a little tough love and hopefully help you avoid some of the same pitfalls!

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Learn From My Mistakes - 8 Years in the Life | WordCamp GR 2014

  1. 1. 8 Y E A R S I N T H E G A M E L E A R N F R O M M Y M I S TA K E S :
  2. 2. W E L C O M E T O T H E L A S T 8 Y E A R S O F M Y P R O F E S S I O N A L L I F E . H I , I ’ M I A N . B U I L D C R E A T E . C O M @ W I L S O N O G R A P H Y
  3. 3. I N T H E B E G I N N I N G … • 1998 - I love PaintShop Pro and Flash, but I can’t understand these weird smudges that appeared every time I saved a jpeg… • 1999 - OMG Dreamweaver is so awesome! • 2000 - Holy crap I can export a table layout direct from Photoshop, now I don’t have to learn code! • 2001-2005 - I hate web development, the bugs never stop, I want to design pretty things with paper. I also want to make comic books. • 2006 - Still not sure about this web designer stuff, but the WordPress default theme has rounded corners and gradients, so that’s good enough for me. • 2006-2008 - Living in in-house designer hell. Please kill me. • 2008 - Bullshitted my way into a real web design/dev job, and so it begins…
  4. 4. H O W T O C L I M B T H E L A D D E R • Bullshit your way into a job where you have to code way above your skill level, in languages you’ve never seen before (love you Ruby). • Design & code for 12 hours a day with your crazy boss lurking just over your shoulder telling you how awful you are at your job while offering no constructive feedback or positive reinforcement. • Stress yourself into an upper respiratory infection and spiral towards a nervous breakdown. • Keep your cool and lay low until your boss has his own nervous breakdown. • ???? • Profit.
  5. 5. O R AT L E A S T T H AT ’ S H O W I D I D I T.
  6. 6. B U T L E T S G E T D O W N T O B U S I N E S S
  7. 7. W H Y I S TA R T E D M Y O W N B U S I N E S S • Opportunity. As the business I was working for imploded, clients who knew and trusted me wanted to go wherever I went. • Avarice. I knew I could make more money doing the work myself. • Ego. I’d seen enough of what NOT to do that I felt pretty confident that I could do a better job. • And a little push. My business/life coach made it clear that now was the time to take charge of my career and strike out on my own.
  8. 8. IS TO DO IT. T H E O N LY WAY T O D O I T,
  9. 9. SO I DID, AND HERE I AM. 
 NOW LETS TALK ABOUT WHAT I’VE LEARNED.
  10. 10. HIRING. L E S S O N # 1
  11. 11. – M E , 
 I F Y O U S E N D M E A R E S U M E W I T H O U T A C O V E R L E T T E R . “…”
  12. 12. T H E PA I N F U L T R U T H • One night, at about 3am, you’re going to realize that you need help. • You’re going to look at the company bank account and look at the money you’re about to start having to share. • Torn between elation at the possibility of getting to sleep, and terror at paying someone to do work you’re perfectly capable of doing yourself if only you had time, you start thinking of likely candidates…
  13. 13. P R O S A N D C O N S O F C O N T R A C T O R S • Pro - Easy to have them work here and there to help you manage your bandwidth. • Con - Their availability is subject to commitments other than yours. • Pro - They’ve seen a lot, and can have a wide breadth of experience. • Con - Hiring a good contractor is expensive. Very. • Contractors will always have their place, the question is how large of a role they play in your business.
  14. 14. P R O S A N D C O N S O F E M P L O Y E E S • Pro - You have much more control over their availability. • Con - In order to retain them you might not always be able to make the most profitable use of their time. • Pro - It sure looks nice to prospective clients having more than a one man show. • Con - You actually have to manage those extra people. • Managing people is hard, even more so when you’re trying to also work yourself.
  15. 15. • Specialization is for insects. 
 Job responsibilities change all the time in a small business, you need people who aren’t one trick ponies. • Your office is going to be a clique. 
 Make sure you hire people that you get along with, or they’re going to quickly feel isolated and disconnected from the management. Feeling isolated when you should feel like your part of a team? Not so great. • Developers.
 Anyone can learn a framework, candidates with a solid grasp of the core language is more useful than someone who hasn’t delved deeper than just working in a platform or framework. • Designers.
 You need someone whose ego is matched only by their willingness to learn and adapt. They need to speak excitedly and confidently about their ideas, but also realize that design isn’t about them, or the client, but rather the audience of the client. • Don’t hire your friends unless you’re prepared to lose them.
  16. 16. CLIENTS. L E S S O N # 2
  17. 17. – M E “Don’t do nobody no favors.”
  18. 18. LEARNING TO MANAGE CLIENTS IS ONE OF THE HARDEST LESSONS YOU WILL LEARN, BUT IT BOILS DOWN TO ONE VERY IMPORTANT SKILL.
  19. 19. SAYING “NO”.
  20. 20. • You, and only you, teach people how to treat you.
 People will insult you, walk all over you, and generally treat you like crap without a second thought. Whether you tolerate it or not is entirely your decision. You are a victim of nothing but your own choices. • Know your value. Literally.
 Working in trade is only advantageous if it’s a fair trade. Always do the math, if it’s not coming out even or in your favor, you are being used. The most egregious offenders are always the nicest people, and it’s hard to say no to a smiling face. This is an emotional decision, not a business one. You aren’t next-door neighbors, you are a business owner, act like it. • Professionalism is extremely rare.
 True professionalism is extremely difficult to achieve and maintain, and as such, is a dying trait. Respect, honesty, candor, maturity, tact- these are the tenets we must uphold in ourselves and are fundamental in forming successful long term relationships. You won’t always get these things in return, but keep your chin up and don’t let it get you down. • Bad clients refer other bad clients.
 If you take on a client you might not otherwise take based on the promise of adding to your referral network, stop and think about what you’re doing. If they have such great connections, why aren’t they more successful? If they treat you poorly and consider that behavior acceptable, what makes you think that anyone they refer will be different? • Expectation is everything.
 Every single person in this room at some point has been guilty of not setting expectations accurately. It happens, and a lot of the time it’s not even intentional! Be conscious of any potential pitfalls or issues that could arise and make the client aware of them before hand. The last thing you want is a client that feels like they’re the victim of a bait and switch.
  21. 21. PROJECTS. L E S S O N # 3
  22. 22. – A L S O M E “This project sucks.”
  23. 23. EVERY PROJECT IS AN OPPORTUNITY TO IMPROVE, BECOME MORE PROFITABLE, AND GROW YOUR BUSINESS. ! THIS IS WHERE YOU TURN CUSTOMERS INTO CLIENTS.
  24. 24. • You, and only you, control the project scope.
 Scope creep. It is the stuff of nightmares. Suddenly your simple project is a towering behemoth poised to crush all your hopes and dreams. Oh and the client is pissed off at you to because now the budget and deadline are both in flux. You live every agonizing hour with the unbearable truth- you did this to yourself. Say no. Or say yes, but it’s going to cost you. • Deadlines are your friend.
 I think the word “deadline” has become tied to the idea of a tight deadline, and the procrastination and cramming that comes along with it. That notion is useless to you now. A deadline is your friend. Schedule your employees’ time around it, base your project milestones around it, your invoicing cycle, etc. It makes things predictable. Set it, stick with it, and it’ll save you all kinds of headaches • Know your role.
 And everyone else’s too. Establishing a clear expectation of who is responsible for what on a project, and having clear lines of communication between everyone involved is critical to keeping a project on track. • Maximize your passion.
 Most of us here are doing this because it’s what we love doing. You know what sucks? When you start to hate it because you’ve been stuck on an awful project for months. Those projects are keeping you from doing the ones you REALLY want to. Say no, regroup, and focus on what excites you. You can make a living AND work on good projects, believe it. • Fake it till you make it.
 A problem I come across a lot, especially working with junior designers, is that if a project doesn’t stimulate them creatively, the output I get from them is rubbish. Even the most mundane projects are a chance to grow your skills. Find the story you want to tell with this design, make it engaging, and let that be your guide.
  25. 25. L E S S O N # 4 YOUR TEAM.
  26. 26. – S T I L L M E “Is it done yet?”
  27. 27. WHETHER IT’S YOUR OWN TEAM OR YOU’RE CONTRACTING FOR SOMEONE ELSE, THESE ARE RELATIONSHIPS THAT CAN MAKE OR BREAK YOU. ! PEOPLE ARE YOUR ASSETS, NURTURE THEM.
  28. 28. • Why can’t everyone just get along?
 Designers and developers tend to have very different, and sometimes opposing personalities, and often get along about as well as bleach and ammonia. They use different words and phrases to convey similar ideas, such that they may be in perfect agreement, but neither can find the words to communicate effectively with the other. Show them how their work makes the other one’s even better, help them to find a common vocabulary, and you’ll be off to a good start. • To remote, or not to remote…
 One of the brilliant things about our industry is the ability to work remotely. One of the most dangerous things about our industry is the ability to work remotely. You have to judge, on a case by case basis, if that person is capable of managing their time responsibly with that level of independence. If they can’t, don’t count it against them. Some people need the structure that an office environment provides in order to thrive. • Autonomy and Mastery > Money
 There was a study done (citation needed, it was probably on NPR) that investigated the connection between employee satisfaction and pay grade. What they found was that there is a ceiling to money’s ability to make an employee satisfied. What brings true satisfaction is autonomy- working under self direction, and mastery- being given the ability to master their chose skill set. Play to your employee’s passions and you’ll not only get awesome work, but happier people too. • Can has communication?
 Different teams thrive in different communication mediums. Some have good luck with collaborative group-chat style systems, some do fine with plain ol’ email. The larger your team, the more important it is to find a communication system that fits within your process. • Who da boss.
 You are. Employees and contractors becoming friends is nearly inevitable. The worst bosses abuse this relationship dynamic. Don’t be that boss. Treat them how you would like to be treated, but remember some day you might have to let them go.
  29. 29. GROWTH. L E S S O N # 5
  30. 30. – M E “Growth is terrifying.”
  31. 31. GROWTH, AND SUSTAINING IT, IS HARD. WITH STRATEGY AND PLANNING, YOU CAN HAVE YOUR CAKE AND EAT IT TOO. ! YOU ARE IN THE DRIVER’S SEAT, DRIVE.
  32. 32. • Planning is everything.
 Do you know how you’re going to handle growth? I think we have a tendency to plan for the worst, but not for when things go a little too well. Growth can and will crush you if you don’t do it effectively. If you can’t reliably forecast your business’ • Upgrading your clients.
 The million dollar question- how do I get better clients? Start with this: analyze your sales data. If you aren’t collecting any, start today. Look at how much time you spending closing low dollar projects vs. a more expensive ones. How does the close rate compare? • Are you happy?
 Growth can burn you (and your team) out, hard. As your business grows, remember why you started it in the first place. Identify the value of the business in your life, and make sure that it stays true to that as it grows. You have to keep your heart in the game if you want to succeed AND be happy too. • Always be closing.
 If you want to sustain your growth you can never. stop. selling. Complacency is the enemy of stability. Experiment. Look for new revenue opportunities in your core business, and look at areas which are ripe for expansion. • Get a mentor.
 Honestly the best piece of advice I can give on growing your business sustainably and being able to actually enjoy the success instead of being crushed by it, is to get yourself a mentor. Some kind of business coach that has been there, done that, and will give you the tough love you will need to survive.
  33. 33. ARE YOU READY? # T H E F I N A L L E S S O N
  34. 34. – I L L I D A N S T O R M R A G E , D E M O N H U N T E R “You are not prepared.”
  35. 35. WHETHER YOU’RE READY TO STRIKE OUT ON YOUR OWN IS A VERY PERSONAL DECISION, BUT HERE ARE A FEW QUESTIONS TO HELP GAUGE YOUR READINESS. ! THE ONLY WAY TO DO IT, IS TO DO IT.
  36. 36. • Are you confident?
 If you aren’t confident in yourself, what you’re charging, and know in your bones that your work is worth it, you’re gonna have a bad time. How are you going to respond to criticism? Complaints over bills? Scope creep? • Do you have connections?
 Do you have any clients ready to go? Colleagues that can recommend you / contract you for work? You need to know people, at least enough to get you started. Connections breed opportunities, and you need to be prepared to capitalize on them. • Do you have money?
 The best part about our business is that the startup cost is extremely low. But you still have to pay the bills. This part is really not fun, but you’re really going to want to make sure that you can pay the bills while you get this venture off the ground. • Do you have a mentor?
 This is the best shortcut to success I can possibly recommend. Just like in programming or design where you really want someone better than you to help tell you where you’re going wrong, the same is true in business. They need to be brutally honest, to keep you equally honest with yourself. Nothing breeds self deception quite like running your own business :)
  37. 37. QUESTIONS? hit me up on twitter @wilsonography

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