Miles Jennings

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Creating a Self-Directed Career

I'm going to MIT tonight for a quick pitch to their students. Yesterday, I was thinking about what I can tell their students about jobs & careers, since their grads have a very different set of issues around their careers than most people. Scarcity of employment opportunities is probably (or more like definitely) not a major issue for most of them.

But what we all share is a need to carve our own path and make an impact, which is what really leads to happiness. I wrote up this handout with some tips to create a self-directed career. It's kind of aimed at young people starting out in their career and looking at what kinds of jobs are out there.

I'm also kind of sick of the cult of entrepreneurship and startups, although I believe very strongly in entrepreneurship. (I know this is not a very logical statement.) But what leads to life happiness in terms of careers is this feeling of ownership, autonomy; essentially liking what you do because you consciously choose to do it. It's important to choose your own path and feel independent - I think that's much more important in the end than entrepreneurship itself, or even than the type of role or company. 

Create GIFs and Everything Else

GIFs. Hard G, soft G, whatever... they're part of our world now. Especially because of Giphy and Slack, Gifs are part of our workplace communication.

Note: I hope that we don't completely lose the use of the English language, but you have to admit: sometimes a Gif says it better than you ever could.

What's interesting is that I've looked at Gifs for years, and used them, mostly for poor comedy, inside of Slack. But I never really thought of creating them. Of course, it's a snap to make Gifs (I recommend Giphy Capture). I'm not sure why I've never made one, or had some made, for my company before.

I think we're conditioned to not create. I think we can often look at something and think, that's nice someone else made that, instead of how do I make that myself? How do I look at Gifs for years and not think, hey I could make one of those for my company. I mean, what is wrong with me?

In any case, I can now look forward to cluttering up the Internet with hundreds of product marketing Gifs in the future. Look out Internet!

We have to remember that the world (and the Gif) is ours to create!


Show that you're going to love what you do

I came across a video on LinkedIn that had gone completely viral - a woman named Page Kemna created a jingle to convince a prospective employer to interview her.

When you see it, you'll know why it went viral - it's absolutely amazing. She's one of these people more than just regularly talented at music; she's fluent in music. She looks like she's fooling around and having fun, but sounds better than the last professional musician you've heard.

Someone should hire her for something. It's an incredible marketing idea, perfectly executed. That being said, my reaction (and my wife's, who was in HR) was the same: "Wow, what an amazingly gifted singer. She should definitely be in music." That might be why her LinkedIn profile still says: "Resume went viral, but still open to opportunities."

The natural reaction is to think that she should be either a professional singer or an independent jingle writer. And I bet she could leverage the virality of that post to create an entire successful career in either of these two areas.

More than anything else, employers want alignmentIf you're hiring a salesperson, for example, you want them to be a little aggressive, love talking to people, be friendly and love helping people, and maybe have a bit of a chip on their shoulder. But most of all, you want them to actually want to be in sales. 

You want to go to a doctor that reads medical journals in their spare time. You want to go to an accountant that crunches numbers in their sleep.

One time a guy I hired to cut down a tree gave me a half hour lecture on the way trees grow to protect themselves in times of drought. It was obvious that he loved trees and cared about his work.  

At the end of the day, you want people whose interests and skills align well with their profession. When you add passion for a job, along with interest and skill alignment, you get those real fantastic career fits, where someone loves their job.

If you're representing yourself to employers, show them that you're going to be good at the job you're applying for. But then also show them why you're going to love what you do. 

Kids think clearly about the future

I had one of those great conversations with my kids yesterday. You know, the kind where you talk for an hour and everyone is laughing and drawing sketches, and generally engaged.

We were talking about the major business models of the Internet over the past twenty years (I know, I know, it's just what I like talking about.)

Kids know better than us. Their minds are clear. I'm not sure that they are more logical in general, but sometimes they have an ability to see things as they are in a way that adults can't.

In any case, we were talking about the greatest business model to come out of the Internet age, and maybe ever - Google. Right now, Google holds the cards. If most commerce happens on the Internet now, it's like they control most of the roads leading to the stores; And they have some patents on concrete manufacturing too. 

We talked about how Google organized the Internet, connecting websites from one to another. To again use the road analogy, it's like they created the signs and paved the roads, so now it seems like they own the roads. 

But they don't.

One of my kids immediately asked, "But if you talk to your computer, are you using Google?" They asked that because they grew up talking to computers, while I didn't. That's what I mean about being clear-headed. Their eyes see the present, while ours can't help but look at the past.

Voice, and the AI technology behind it, is much more of an existential threat to Google than Facebook ever could be. Facebook mastered the social graph and this does, in some ways, created a new paradigm for finding services. Meaning, you can ask your friends instead of asking the web. 

But this isn't the real threat. Facebook still plays in the same world of websites and apps, the world of the 1990s. I don't think it represents the paradigm shift that voice and AI represents. These new technologies could destroy computers themselves. They could destroy mobile devices. It doesn't change what we do with computers or browsers - it makes computers and browsers irrelevant. This is why Google is dumping money into AI and voice technology.

For right now, Siri, to use one personified AI assistant, is pretty darn stupid. I tried asking Siri to open "Robot Unicorn Attack Two," and she couldn't do it. She needed to hear the actual name of the app, RUA2; even though it's "her" own app, in her own app store, on her own device. 

The robots have a long way to go before they attack.

The challenge for us thinking about technology, and also how to raise kids that know how to best use technology, is to think clearly about the future. To see the present for what it is and not through a lens of how it was. 




After a Couple of Weeks (Almost) Facebook Free

When you use Pandora over time, it starts knowing you a bit too well. You start hearing the same music over and over again. You aren't challenged anymore. You feel spoon fed or frozen in time. The AI engine gets lazy.

I noticed this recently with Facebook. People talk about the "echo chamber" of Facebook - it starts predicting your likes and interest, and then simply feeds you that. It feeds off everything that is you - or at least what you are now, and not what you want to be. At it's heart, it's an advertising matching engine, distilling your desires and interests into commercial intent.

At the same time, I saw myself using Facebook too much, mostly at night. It's designed to keep you hooked, and those thousands of software engineers know what they're doing and do it well. 

It was too much - and I started seeing it as a destructive aspect of my life.

Probably like many people, I use Facebook for a lot more than sharing pictures of my kids. I have company pages that I administer, ad accounts that I help manage, and a couple of really valuable groups. Deleting Facebook for real isn't really possible for me. 

But the real issue, for me, is the app. Deleting the app segments your time spent generally to the day, and the net effect is almost the same thing as deletion. After a couple of weeks (essentially) without Facebook, here are some of the things I've noticed:

- You talk more to people - because you have to. Facebook lulls us into a sort of relationship complacency. You feel like you know what people are doing, so you don't need to ask. Of course, Facebook updates are never how people are really doing, that's just their highly curated blend of what they want the broad world to see.  

- You haven't heard of everything already. People are so hooked on their feeds that a lot of conversation these days are things people gleaned from Facebook. Starting sentences with "Did you see that thing on Facebook" has to be one of the most common expressions. When you don't use Facebook as much or at all, there's a gap: you haven't seen every meme.

- You go to old media a bit more. Facebook has the most up to date, comprehensive news aggregation service out there. Without that as your starting off point, I find myself going to newspapers and magazine sites a little bit more, where you get editorial versus algorithmic spoon feeding of content.

- You have an extra hour. Maybe this is just me, but I believe I'm getting an extra hour in the day by not having the Facebook app. I started spending much of my last hour before going to sleep checking Facebook, reading news, and seeing what my friends are doing. Without that, I feel a bit like I'm getting a 25 hour day. Now to make the most of it!

I can't think of anything negative about killing off Facebook time. Maybe if there is a bear attack in my neighborhood, I won't hear about it until it's too late. I'm guess I'll have to take that chance.


Talking to Kids about Business

This is a topic I enjoy thinking about... how do you talk to your kids in the right way about business? I got a lot of helpful input from other members of the YEC group that also have kids. 

Here's How Entrepreneurs Are Talking to Their Kids About Business

While it is very true that children often do what you do, not what you say to do, it’s important for parents, particularly entrepreneurial parents, to give their actions context and pre-empt that favorite question of all children: “But...why?” This way, not only do children understand the hard work you put in -- and why sometimes you have to leave them for a bit -- but they become empowered to see possibilities of entrepreneurship, even at an early age. Just by taking a few moments to reflect with them on a universe of possibilities, you can create avenues for greatness.


Chief Evangelist

Good ol' grand-dad Luke the Evangelist! My 23andme report says it, so it must be true.

This is yet another reason for me to add that annoying "Chief Evangelist" title to my Twitter bio. Turns out, it's in my blood!

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Go to Bed Mad

We're taught to "never go to bed mad" with our spouses. But the reality is that we often think better in the morning. Many times, we won't even remember what we were mad about.

When you're running a business, you can expect to deal with problems - a lot of problems. You're everyone's go-to person for problems. 

If there are issues with an employee, you worry about how it will affect your client relationships, for example. It's easy to work yourself up about things - grind away at the issues and try to resolve everything in your mind. It's a recipe for frustration.

It's many times better to let things go... resolve what you can through immediate communication, but then try to only care about the things that you can change. Worrying doesn't help resolve anything, and it's many times better to sleep on things.

I've learned to compartmentalize things in a way, to just do everything I can every day, but then let the things that I can't change drop. Or at least let them rest until another day.

It's many times good advice to "go to bed mad" at your spouse. To say, "Hey, I love you, but we're both tired, let's go to bed" - to address things fresh in the morning. 

Same goes with business - stewing in worry makes everything worse. Do what you can each day, and let the rest go. Resolve what you can quickly, and then move on to other things where you can make an impact.

Trust that each morning everything will again be new.


Yet Another Human Driver Kills

After a self-driving Uber powered car recently killed someone, the state immediately moved to put the brakes (no pun intended) on further testing of the technology.

The first death caused by a self-driving car is certainly a watershed moment and should give everyone, including the company, pause. If we call this beta testing, we just uncovered a critical bug. The bug has to be fixed, fast and entirely.

However, I can't help but call attention to our very human reaction to this inhuman error. We are highly susceptible and influenced by headlines.

"SELF-DRIVING CAR KILLS" sounds pretty scary. Yet in every local paper, every day of the year, we could also publish: "YET ANOTHER HUMAN DRIVER KILLS." 

We are biased against the new, even if that new produces results factually much better than anything before it. Headlines are biased against the outlier, because when a member of the largest group does something of note, we don't call attention to their group membership.

It reminds me of people calling to end homeschooling because of one lunatic family. We don't hear headlines about public-schooled families abusing their kids, because there is no reason to identify them as public-schooled, which is the largest group. 

Let's remember not to kill the promise of a better future because we're biased for the past and against the outlier. Let's look at data to solve our problems. Self-driving cars hold the promise of ending what is one of the major causes of injury and death. It's one of the recent innovations which holds the greatest potential for good.

To use another car analogy, let's turn the light yellow, not red.



Don't Worry about the Wrong Questions from Investors

When you meet an investor in-person, they'll usually A) be extremely helpful (it's almost their business) and B) ask lots of great questions.

B (the great questions) is a lot of what drives A (the helpfulness), as the right questions make you think about your business in a different way. The right questions may be challenging, but they are also a vital process for growth. 

If you have no one challenge you, you can't grow, and your business stagnates. As a rule of thumb, investors are a savvy lot, and fill that role of challenger.

One thing to know is that some investors and investment clubs use automated screening programs to weed out valuable startups. Programs like Gust give investors the tools to ask up-front questions about your business.

The automated questions are where things go wrong.

I remember one time that I was applying through one of these automated screening platforms. One of the questions was this (I believe I'm quoting this right, as it was years ago):

"Can your technology be characterized by the presentation of fields, that a user completes, which then causes workflow events to take place because of the content of these entries?"

I kid you not.

Now that's a doozy of a question. It's meant to screen out companies that are not pure technology in the highest sense. 

However, it's also a terrible question. Especially in the first few years of their existence, Uber fits this broad characterization, as does Facebook, Quora, Yelp, and Angie's List. They would have been screened out.  

Take investor input seriously. Consider their questions and criticism carefully and learn from them. But don't take every question to heart, especially feedback or questions that are driven by automation instead of discussion.

Not every company is right for every investor, and not every investor is going to be right for you.


All Anyone Cares About Is Your Network

The old model of distribution consolidated power in the hands of media companies. Newspapers, movies, books, and television were (really broadly speaking) the only way to reach an audience.

Social media changed all that, kind of.

In the modern method, the media companies still have consolidated distributive power. However, the source of that power is less about their organic authority and more about combining networks of contributors into nodes of influence.

For example, we have contributor-supported content models, such as Forbes Contributed content. We have Yelp, supported by contributed reviews, versus the old model of professionally written reviews.

End result: powerful companies are still very powerful, as they are the best at synergistically bringing networks of influence together.

Without working with established brands, distribution to an unlimited audience is theoretically possible, but not usually probable. You can even make the argument that decentralization of distribution made brands more powerful, as our attention is fractured and pulled in many directions.

This is old news, really.

My thought today though is how this changes the power dynamic when negotiating with brands that used to represent distributive power itself. If you are looking for a book deal from a publishing house, for example, the first thing the publisher will ask is “Who can you promote this to?” 

You’re thinking, “I thought that was your job.”

If you work with a crowdfunding site to raise money, they will tell you, “We’ll give you the tools you need to promote this deal to your network.”

You’re thinking, “I thought that was your job.”

End result: companies that used to promise you an audience or customers now ask you for the same.

Takeaway: Develop your network and audience, no matter what industry you’re in. An audience is now a prerequisite for working with larger companies; the mobility or portability of your network is the largest determining factor in your value. Oprah can bring her audience anywhere; can you?


3 Things People New to Recruiting Should Know

I was asked to speak today to a group of people getting into the recruiting profession for the first time. This is part of a course on how to be a recruiter offered by This is a subject near to my heart, because sales and recruiting was really my first job after college that I really put a lot of effort into. 

Here are the things that came first to mind for me, and what I'm going to go with when I speak with the group.

  1. Don't be afraid. It's easy to be intimidated by smart candidates. It's easy to listen to people who denigrate recruiters. It's easy to forget that you're offering a valuable service. All of these things can make new recruiters not want to network, not want to talk, not want to pick up the phone. It's critical that you do what you have to do to get over these fears. Read some motivational books, get yourself psyched up, and learn to enjoy rejection. Make it a game and don't let yourself get down.
  2. It's a numbers game. Like sales, recruiting is basically a funnel. You need to put a lot at the top and watch it trickle down. The # of calls and outreach you do turn into discussions, which turn into submittals, which turn into interviews, and interviews turn into hires. No matter how "good" you are at qualifying, you need to do a lot of activity and put in a lot of work at the top of the funnel. It's also important to not screen too many people out of the top of the funnel, as you need to get activity going.
  3. Your time is precious. Everyone's only real commodity is, of course, the time that we have on this earth. However, when you're recruiting, you realize that your only professional asset is your time. You don't want to waste time with bad candidates. You don't want to waste time with bad clients. Success is most directly tied to how you delegate your time - what you spend your precious time doing. Don't spend time pushing things to happen that cannot happen, such as pushing the wrong candidate for a particular job, because this just hurts you. You have to be extremely "greedy" with your own time, and learn to say no.

When Something Works

With startups, effort is everything, but you have to be putting your effort in the right place. A reminder to myself: when something works, do it more. When something doesn't work, don't do it again or change the process entirely.

When something works really well, figure out how to multiply that activity by 100 or 1,000. Find an activity that converts into a positive outcome then create a repeatable process. If you have the capability to do that activity many times over, that's when you can achieve scale.

The question of what works is interesting (that's 1. market testing/validation), but the question of how you can multiply that positive activity many times over is exciting (2. system thinking/scale). You want to design systems that compress the decision-making process of steps one and two as much as possible.

Ideally, you want to discover what works quickly, and then quickly determine how to multiply what works.  

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Give Yourself the Win

If you love goal tracking like me, you know that the hardest part about achieving long-term goals is being consistent about completing the daily tasks and actions required to meet the goal. 

But when do you give yourself that "completed" checkmark on a task? Even personal things like: Read every day. What counts as reading? Is it reading a chapter? For half an hour? Exercise 3X/week. What counts as exercise? Is it 7 minutes in the morning or does it have to be a half hour run?

Today, I think that it's important to give yourself the win, even if you achieved only a tiny bit of traction: cut yourself some slack, but demand consistency. Expect daily progression from yourself. Small actions compound over time. Do small things toward a big goal, and be happy to complete daily goals, no matter how small.

BTW, I enjoy the feeling of writing out goals with pen and paper, as you can almost feel the neural pathways burning in deeply as your brain tells your hand to write. A big hat tip to Best Self journal, which is the most expensive notebook I've ever seen, but is an excellent product and worth every penny.

Don't Worry Too Much About Brand

So Wal-Mart is now officially Walmart. It took them decades to remove that hyphen.

But at your startup, you're spending weeks thinking about your brand name and the precise hex code to use for your website and logo.

Meanwhile, Walmart is just selling stuff, lots of stuff - executing.

The point being, one mistake I've made in the past is to worry too much about little things. Get the basics: have a name you like, a snappy website, grab some business cards on Moo. But don't obsess over stuff that at the end of the day matters little.

Brand is important, but it's a lot less important than getting stuff done.

Feeling is Everything

Today I reviewed a new explainer video for VocaWorks for design. Something really hit home: the overall emotional feeling is everything. The graphics, layout, voice, presentation, etc... all flows down from one point of emotion, and if that point is wrong, then you can throw everything else in the garbage. I'm going essentially for "exciting growth" and what was conveyed was "frustration".

When designing software or marketing materials, you want to first really nail the emotion that you want to convey.  Everything else is informed by that. I also don't think that this basic overall emotion can ever be a negative emotion, at least for a commercial product. Or at least we have to be really careful to ever put negative stuff out there. "Yeah, that's a bummer" is never a good emotion to put out in the world, either through our own personal interactions or our company messages.


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