Leap First – Jennifer Bachelder

April 14, 2016

jennifer-bachelderEver met someone who instantly changed your perspective and got you to see the world in a new way? It doesn’t happen very often, particularly for stubborn assholes like me.

But Jennifer Bachelder tiptoed right in there and did something to my brain. It was sneaky as shit.

It started with the most simple of things. We met at Starbucks. I ordered an iced tea. I took the straw out of the wrapper.

Without realizing it, I proceeded to do this nervous twitchy thing that I have probably been doing every single time I have ever been with another person at Starbucks since the beginning of time.

I wound the wrapper around my finger and then unwound it, over and over, maybe a hundred times. Considering all the times I’ve been to Starbucks and ordered an iced tea, I’ve probably wrapped that thing around my finger tens of thousands of times. Maybe hundreds of thousands of times.


At one point in our conversation, Jen picked up the now curly wrapper that was sitting on the table and asked me, “How many people and how many hours went into making this?!”

I didn’t have an answer.

She proceeded to list out for me all the things that probably had to happen to bring that wrapper to fruition. People deciding on the color. People approving the decision to spend more on something in color instead of black and white. People approving the color to make sure it was consistent with the brand. People approving the font. People choosing the words that would be printed. It’s a cautionary message, so legal probably got involved…

The list went on. All this money, energy, and people’s time spent on some little thing that ends up in the trash… or is mindlessly wound around someone’s index finger a hundred times and then ends up in the trash.

I had never seen anyone speak passionately about a straw wrapper before. I probably never will again.

Well, for me, it started with that wrapper, but then, like a virus, it spread. I started noticing shit. All over the place, that day and since, I was noticing stuff I never would have noticed.

Now it turns out, Jen has a soft spot for trash, and I’m not her only victim.

In college, Jen majored in graphic design. In one of her classes, the professor did something that hit her hard, probably harder than she even realized at the time. After everyone submitted their final projects, something they had all worked tirelessly on for all this time, he walked around the room with a trash can and made every single person throw their project away. He was teaching everyone a lesson about where a lot of their work was going to end up given their chosen field of study.

Since then, Jen has paid attention to things that end up in the trash.

Fast forward some years: Jen was getting a lot of junk mail in her post office box. She started turning the junk mail into postcards that she would then send to her friends. She got a kick out of turning that trash into something and then having the post office deliver it all over again. (Eventually, that turned into a side project in postcards, which later expanded into designing calendars—first as gifts for her graphic design clients, but pretty soon she was selling more of them than she was giving away.)

And then there’s her studio art. She focuses primarily on turning garbage into art. That happens to be the opposite of my usual approach, which is to try to make art but instead to make garbage.

Here’s an example of her work. One person’s trash is another person’s…


These days, Jen’s friends are now all well-aware of her soft spot for trash, so they’ll save trash they think she might like and will give it to her, which made her think… If I’m even making people take notice of trash for one second before throwing it away and having it end up in a landfill, perhaps there is something meaningful there.

It’s quite the evil plot to infect innocent people like me. It worked. I’ve already sent hate mail to her college professor, made out of some torn up credit card offers and the flyers for lawn care services that get wrapped around my front door knob on a daily basis.

But let’s back up. Because what first attracted me to Jen’s story was something entirely different.

Not too long ago, Jen had a “regular job” at a marketing company as an “Event Producer.” There she was—a graphic designer by training and someone who probably would’ve pursued studio art if she was “more of a risk-taker and had more confidence in [her] studio art skills”—but she was doing events. And she was doing them for a Horrible Boss. (My words, not hers, so send the hate-trash-mail to me, not her.)

She knew she had gone off track. Fear had gotten the better of her.

It wasn’t always that way. Her ideal job coming out of college was to design album covers for a record label. She snagged an internship doing just that at Invisible Records, an industrial metal record label. To make ends meet, she did part-time work babysitting, she worked in a flower shop, and she slept on her friend’s couch.

After some time, Jen decided to take a job at this marketing company. She started off doing both graphic design and events. But after a few years, she was promoted to the head of the events department. In this role, she worked for a boss who cyclically went through episodes of projecting all of his problems onto everyone around him, and then firing a bunch of people.

Jen knew it was time to move on. It wasn’t just the boss. The problem was that her artistic passions and freelance design projects were being crammed into the tiny windows of free time she could scrape together during nights and weekends, whereas she was spending the vast majority of her best waking hours working on something for someone else that just didn’t excite her. And she suffers from what I call Overachiever Syndrome—the inability to do B+ work. She pours her heart into everything, even if it’s not really what she wants to be doing.

So Jen did something a logical and pragmatic person would do, and she put together what I will refer to as a Super-Practical-Six-Month-Plan to save up money and make the leap into doing her passion full-time—her graphic design and studio artwork.

If you ever find yourself in a similar situation—working a day job you don’t like while pining for a full-time career doing something you love—I encourage you to reach out to Jen for advice on the nuts and bolts of assembling your own Super-Practical-Six-Month-Plan. I am also proposing that she share the secrets of her plan-writing approach in her own blog post, so please send her lots of emails and trash-mail to encourage her to write it. Eventually I will link to it here. (Not a real link yet. Get on the emails and trash-mail, people. )

In the meantime, I’ve distilled the essence of her overarching approach into a few key steps, which are as follows:

  1. Get out a pen and paper
  2. Write down a super practical plan for how to save up enough money in six months to leap from your current job into the freelance or creative profession of your dreams.
  3. Spend one extra second taking notice of this piece of paper before dumping it into the trash.

Three weeks after Jen hatched her master plan, she and her boss had a “disagreement.” Given her definitively warm, witty, infectious personality as certified by me, I can only guess who may have been the instigator.

But when the time is right, the time is right. Even when the time isn’t really right according to the plan you put together and sent to the landfill.

So Jen abruptly quit, moved back to where her family lives in Columbus, Ohio, and rented out half a duplex from her new landlord, her younger brother.

One of my favorite people, Seth Godin, gave a talk I highly recommend that was recorded as an audiobook called Leap First. (It was also turned into a print book.) I think “Leap First” is an appropriate tagline for Jen’s journey. And I think Jen is a living example of why this can be an effective approach for pursuing one’s passion or purpose.

Now, my lawyers are telling me to include a disclaimer: I am not responsible for any loss or damage should you choose to follow this “Leap First” approach. My lawyers also wanted me to remind you not to drink your hot Starbucks beverages through a straw, because you could get hurt, and the plastic might leach.

Here’s the thing with Jen’s leap. I am not pretending it’s easy for her. She is clearly working her ass off. She hasn’t grown things to a point where she can turn down work at will, so she has been forced to work with difficult clients she’d prefer to fire or to do work that isn’t always what she would prefer to be doing. To supplement her income, she currently allows a revolving door of strangers into her home by renting out part of her place through Airbnb. (Although, ironically her place is super close to an Airbnb call center, so it’s become a hotspot for Airbnb employees, who happen to make very good Airbnb tenants.)

And self-employment ain’t easy in other ways, particularly when you’re early on and working your way up. Some days it takes its toll on Jen in terms of finding time for things like self-care, whether that’s getting enough sleep or squeezing in a workout. And there is inherent uncertainty, like clients who don’t pay on time or the risk of clients who might not pay at all.

But compare her life Now with her life as an Event Producer. She is currently working about 30 hours a week freelancing as a graphic designer for a few primary clients. (Interesting side note, one of her clients is Victor Saad. Victor started something called the Leap Year Project, which is more than one hundred percent relevant to this story, if it was possible to get above one hundred percent anywhere other than in a high school coach’s pep talk.)

Jen also gets to do studio art. And she also has a budding business doing projects like wedding invitations, along with the postcards and calendars I mentioned earlier.


In this new life of hers, she has designed a “slash career” (as in I’m a doctor/actor or I’m a singer/author/stay-at-home-mom) that many of the artists I’ve profiled have also had in their own way. And in Jen’s case, all of her slashes give her something unique that she values besides just being a job that pays the bills.

Studio art is about creating something for herself. Graphic design is about bringing a client’s vision to life. Studio art is a solitary activity, whereas graphic design gives her much needed people interaction and the associated creative inspiration that helps keep her studio art fresh. She doesn’t actually want one of these two to win out; her ideal mix would be an even split between the two.

And she’s really good at what she does. She has a gift very few people have when it comes to client work. I got a taste of it and she probably didn’t even realize I was certifying her services.

While we were at Starbucks, we talked about this promotional piece that was sitting on our table advertising Starbucks’ music playlist. Jen asked me a bunch of questions about it, like how various elements of the promo piece were working for me, what I thought Starbucks really wanted to accomplish with it, and so on. By the end, I came to a completely definitive conclusion about this thing all on my own:  It was an utter piece of shit.

This being the internet, the person who designed that thing for Starbucks could read this someday. I apologize in advance, Sir or Ma’am. I know you were probably under a tight deadline and your boss or client didn’t communicate clearly what they wanted and the budget was probably too small and probably a bunch of other stuff too. But it didn’t get the job done at all. Again, Jen got me to see things in a completely different way. I’m now a client of hers, and she doesn’t even know it yet.

It would’ve been so easy for Jen to get stuck in her Event Producer job. She could’ve easily waited those six months to get all her ducks in a row before taking the leap. And what’s a couple more months after you’ve waited six months? And what’s a couple more after that?

I’ve seen that movie before. I was in that movie before. I had one line, it was “I’ll just wait until the end-of-year bonus, then I’ll move on.” I delivered that one-liner convincingly. And then three years passed by. It was a long movie, way longer than Braveheart.

Had Jen waited to take the leap, I think she would’ve suffered because of it. I know the world would’ve suffered because of it. Her real creativity would’ve been confined to the slivers of time she could scrape together when she wasn’t pouring her best hours and energy into something she didn’t enjoy.

Now, a lot more of her time is spent doing what she enjoys and putting that out into the world. And even without the well-executed plan and the six months of savings, she is finding a way to make it work.

That’s the beauty of leaping first.

Obviously it’s easy for me to tell you to just go for it, because I’m not you, nor am I your family. The difference between me and those people is that I actually believe in you in a way those people might not. We may not have even met yet, but I believe in you. I know something you don’t know about your ability to get shit done when it’s doing something that’s authentic to you.

So do something you love.

You don’t even have to “leap first.” That’s not really the point. Keep your day job if you like.

But do something you love.

You don’t have to listen to me, of course. You can listen to Resistance if you want. You can listen to all of those other people who will tell you to play it safe. You can listen to fear and anxiety.

I gathered Jen’s mother pretty much shat a brick when Jen quit her job. Jen’s father probably would’ve loved to see her be a math major since it turns out she’s pretty awesome at that too, but that ship officially sailed by the time she hit college. She also has some brothers, one of whom routinely sends her pictures of “Help Wanted” signs, the most recent being from the window of a Chipotle. I assumed he must have been joking with her, but it turns out I get things wrong now and then. In Jen’s words, “Well, at least he’s thinking about me.”

But do you love math? Do you love working at Chipotle? Do you love being an Event Producer?

Or do you love graphic design and studio art. (Or whatever your thing is.) I left the question mark off because that was rhetorical.

It might appear as though I’m making all of this sound easy, even for Jen. But Jen was very clear with me. There was nothing easy about this. There still isn’t.

She regularly battles with the creative person’s biggest enemy but often their most common visitor… lack of confidence and feelings of vulnerability associated with sharing her work with other people.

She regularly battles all the other forms of insecurity inherent in self-employment.

She also had to move through the fear of the leap itself, which she said was “Terrifying.” More importantly, she told me, “It’s still hard and it’s still terrifying. Once a week I get terrified.”

And that’s because you can’t know what will happen. But you knew that.

And it’s because there are no guarantees everything will work out the way you want. But you knew that too.

And it’s because it probably won’t be easy for you. Nobody ever said it would be easy, not even me.

But which do you want more, something easy or something you love?

You might not get to have both. But it’s your choice, it really is. So which is it going to be?

♦ ♦ ♦

There is a leap of faith in everyone’s story. Sometimes it works, sometimes it doesn’t. Read the next story to find out why in How to Win an Emmy



In a generous mood? Share this post with anyone you think needs a kick in the pants to go for it in life. 

Thank you Jennifer Bachelder. I’m a new believer in the art of the impractical. I’m also acutely aware of even more of my idiosyncrasies, and I’m more responsible about trash, too.

Check out more awesomeness at jenniferbachelder.com.


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