Josh Simmons

Community Manager at O'Reilly Media

Latest Posts

Life After Wimptator

Posted on by Josh Simmons

Melissa and I first met at A’Roma Roasters on Wednesday, April 6th, 2011. It’s easy to remember, because the WIMP meetup was registered on the same day. That’s probably the first sign that we were going to kick ass. Since then, WIMP has changed Sonoma County: it’s a far less lonely place to be a technology or media professional now than it was 5 years ago.

WIMP has changed me, too. For all my labors of love, none have been as enduring or meaningful as WIMP. The friendships I forged, especially with Melissa, Randy, and Cole, are ones I can’t imagine living without.

Now it’s time for more change. After four and a half years, it’s time for me to step down from WIMP leadership. Deciding to resign is one of the hardest things I’ve ever done, which I recognize makes me one of the luckiest guys alive. But giving up your baby is hard, especially when it’s doing so well.

First trace of Melissa in my life is a comment on this photo Philip Wyers posted to Facebook in 2010. Nerd humor FTW.

I have spent the better part of my adult life as a scrappy careerman trying to overcome circumstance — and myself. While the journey continues, my time as a careerman has to end.

I still have ambitions to leave this world a better place than I found it. Hell, I’ll still be a big WIMP supporter. But my priorities have to change… As I approach my 30’s, I want to spend more time with my family and friends. I also want to think about building a family of my own.

And WIMP is growing up. What WIMP needs now is different from what it needed to get started. While I’ve got some skills, I’m no CEO — I learned that the hard way with my startup, Bluebird.

In closing, I just want to say thank you. Thank you for the support. For the creativity. For the love. I’m sure I’ll see you around.

Your Wimptator emeritus,
Josh Simmons

Be Your Business: Don’t Forget to Fail Well

Posted on by Josh Simmons

Adversity: The New Normal

It happens. Things go south and it’s not even clear how. Your client and you can’t see eye to eye, or your enthusiastic new business partner has dropped off the radar. The project you’ve invested weeks, months, or years into may never see the light of day.

Failure comes in many forms and the increasing complexity of our projects and the world they operate in doesn’t help. Despite our best efforts, learning the hard way is often the only way. Perhaps this is why modern startup culture has rallied around the mantra: “Fail fast. Fail early. Fail often.” But I spent the better part of my career failing, and the experience leads me to believe the common refrain to be lacking.

Like gymnasts who train to fall properly, I believe we must learn to fail well. Something I never did. It took me 12 years and spectacular failure as a freelancer and as a startup CEO, but I think I’m starting to learn the art of failing well.

Don’t Make Things Worse

Here’s the framework I use. I hope it helps you remain lucid in the face of failure and, FSM willing, makes your next failure a little less painful.

  • Managing Yourself: Stay calm. There are plenty of fish in the sea. Mindfulness meditation, hikes, and frequent visits to the beach helped me through my most challenging failures. We can easily be our worst when things get rough, so proactive self-care is fundamental to failing well.
  • Managing the Relationship: Failure tests relationships with coworkers and with clients. Do not seek blame - most failures are collaborative - but do a post mortem. Your goal is first to establish a conciliatory, productive, tone, and only then dive into the nitty gritty of resolution. Be generous. Learn to apologize well. And, when appropriate, cut your losses.
  • Managing Your Reputation: Do not bad mouth former clients and coworkers. Learn to tell your story without peppering them with mitigating factors - they sound a lot like excuses. But actions speak louder than words, so focus on doing good and learning from the failure.

Those should help you think through your next rebound. But I’d be remiss if I left you with advice only in the abstract. I have stories and practical applications of the above framework in depth, and I’m happy to share my wisdom.

Upgrade to Better Failures

I will close with my list of the top 10 freelance pitfalls. Do your best to avoid these, or at least learn from them!

  1. Fail to Measure: Do not put this off. Do not believe the voice in your head, you should be measuring even if you don’t “have to.” Track your time. Watch your cash flow. Without data, both your business and your welfare is subject to the winds of intuition. With data, you can build ever more precise estimates and craft ever more lucrative proposals.
  2. Work Without a Contract: I don’t care if you are BFFs or married to your client, you need a contract. Even if money is not changing hands, a contract brings clarity to critical issues like ownership of intellectual property, communication standards, and warranty/maintenance. Don’t want to pay an attorney? Look online for templates, or just write a “Memorandum of Understanding” in plain English and have both parties sign it.
  3. Over Commit: It seems obvious but we humans are skilled at overestimating our own abilities, so it bears repeating. Of note, it is shockingly easy to over commit if you have failed to measure and do not know either your capacity or the current utilization of that capacity.
  4. Give it Away for Free: Pro bono work is good. But ask for a recommendation, referrals, or a case study. Even if your invoice shows a 100% discount, send that invoice. And if you’re doing a free consultation, remember you’re there to build a rapport, not to instruct your lead on how to provide the service you are offering.
  5. Surprise a Client: I’m not talking about flowers or wine here. I’m talking about failing to set expectations, or over promising then under delivering. People are more forgiving than you think, so alert them at the first sign of danger. Nothing is worse than radio silence.
  6. Do Everything: Don’t be everything to everyone. Even generalists need a specific hook. Consider subcontracting for things that aren’t central to what you offer. For instance, don’t do your own taxes just because you can. Your time is more valuable than that.
  7. Be an Island: You cannot learn all of the things, and there’s no better way to find new opportunity than to meet new people. Engage the world around you, seek community online and offline.
  8. Work Yourself Out of a Job: Sure, you didn’t choose a creative profession just to find yourself doing sales. But if we only engage in our craft, one day we’ll finish a project and go white with horror as we realize we don’t know where the next check is coming from. We must learn to juggle promotion and production.
  9. Put All Your Eggs in One Basket: Failure is inevitable, but diversity builds resilience. Don’t set yourself up for catastrophic failure by having only one client, or one marketing channel, or one pitch.
  10. Lose Touch with Your Clients: The easiest way to grow your business is by selling more to the clients you already have. Stay “top of mind” with a newsletter and cards for birthdays or holidays.

I’m sure there’s a lot I’ve missed. What advice would you add?

Community Survey: Measuring the Might of WIMP!

Posted on by Josh Simmons

It’s time for WIMP to take the pulse of our local creative economy. Our little community isn’t so little any more, and while the WIMP leadership (your “Wimptators”) feels in tune with our group, intuition doesn’t scale the way real data does. We want to better understand our demographics, benchmark our progress and, perhaps most importantly, shine a light on the tricky issues of compensation and contracts. That is why we are in the midst of conducting our first annual Community Survey.

Where WIMP Is Now

Discover whether you’re leaving money on the table, or perhaps that you’re charging as much as the market can bear.

The WIMP community is now over 800 people, mostly in the North Bay, 50% of which are freelancers. Yet, many local businesses needlessly send contracts for web development and design out of county and out of state. And freelancers, a population that is projected to outnumber regular employees by 2020, still don’t factor into long-term economic policy, school curriculum, and government reports on employment.

By taking our survey, you help us change that. While we know we’re playing the long game here, this survey will also deliver short-term value, and not in an abstract hand-wavy fashion.

In early 2015, we will publish a report based on the survey responses. That report will be full of useful information, but there are two things everyone is expecting to see:

  • How much people charge, and,
  • An analysis of modern creative contracts.

Money is the real elephant in the room, especially for freelancers and small agencies. It is impossible to know what is fair and what is competitive without sharing data. And sharing pay data in-person can be risky, not to mention uncomfortable.

Enter WIMP’s Community Survey, which we conduct anonymously in order to protect your privacy. And since we are surveying freelancers, employees, students, professionals, business owners, designers, developers, marketers and other creatives, we can correlate compensation with context.

Why You Should Care About A Survey

The report and analysis will help you figure out where to set your rates. You can discover whether you’re leaving money on the table, or perhaps that you’re charging as much as the market can bear. However, that insight is impossible without this survey and your participation!

And how about those contracts? I am not a lawyer (IANAL), but I think it’s safe to say that boilerplate contracts are generally terrible. Templates available from reputable trade groups like the Graphic Arts Guild (GAG) are passable at best.

We live in a mixed media world and our contracts should reflect that.

With your help, we will put together tailored contract templates that reflect the needs of a modern digital media professional. For standard clauses such as payment, termination, and arbitration, we want to find the best of the best. And we want to craft state-of-the-art clauses for things you may not have considered including IP transfer, warranty, maintenance, and more.

The Rising Tide

All of our ships rise with this tide. Please, take a few minutes to answer our survey and also share it with friends and coworkers in the industry. Whether you’re a “WIMP member” or not (you probably are), whether you’ve been to an event or not, whether you’re based out of the North Bay or not, we want to hear from you.

Help us make 2015 the year we stop running our careers on guesswork. Let’s make some data driven decisions!

WIMPgives 2014: Wimps give $75K worth of services to local nonprofits

Posted on by Josh Simmons

Northern California nonprofits, rejoice! Our annual tradition of giving continues this year with WIMPgives 2014. Last year we mustered over 24 volunteers to build websites for five local nonprofits. This year, we’ve rallied 50 volunteers to make it happen for seven - with added strength in the marketing department to make our impact last even longer.
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WIMP for the World - with Your Help

Posted on by Josh Simmons

“Ask a person, not a search engine” is our tagline here at Web & Interactive Media Professionals (or, as we say: WIMP) which is a Sonoma County, California unnetworking group with big ambitions.

Founded in 2011 by a freelance designer (Melissa) and developer (me, Josh), our goal was simply to find likeminded folks in a place with much less density than San Francisco or Silicon Valley, but not far from them.

But we’ve since ballooned into a group of over 500 designers, developers, marketers, and other media professionals, and we’re quickly evolving into a full fledged trade group.

Better yet, we’ve found that our approach really is unique - one member captured it well when he said WIMP is “a local LinkedIn that doesn’t suck.” We have a casual approach to professionalism and bring together a variety of skills, creating a rich dialog and solid relationships without the pretense of a networking group.

By combining a diversity of disciplines we become more well rounded craftspeople, help people find their niche, and generate substantial outcomes in terms of job opportunities.

And we’ve hit a tipping point. We’re at a point where we need more than just our co-organizers spare time to really meet our community’s needs.

We have hosted over 70 events and barely any have been recorded, much less live streamed. And we want to roll out premium memberships to help underwrite our transition from meetup to trade group.

But to do that, we need to be a proper business and processes to ensure that we remain accountable to our community as we grow. That’s not cheap.

So we’re asking for your help. We are trying to raise $15,000 by May 10th so we can immediately begin recording and streaming our events as well as begin laying the foundation for our evolution.

Have you learned, earned, or made friends in WIMP? Pay it forward today and come celebrate our campaign’s closure with pizza and good times at our Crowdfunding Countdown.

Already 33 people have put their money where their mouth is, donated, and gained charter member status. Thank you for doing your part and making WIMP what it is today!

Your co-founder,
Josh