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I Failed Buffer’s Bootcamp…Successfully

Sep 21, 2016 8 min readWorkplace of the future

Heads up! This is an older post that references some outdated processes at Buffer, specifically the “Buffer bootcamp.” Feel free to see the latest information here, including all the reasons why we retired this concept!

We’re Retiring The ‘Buffer Bootcamp’ Period For New Teammates – Here’s Why

Every new person who joins the Buffer team starts with a 45-day bootcamp trial period, which is intended to see how the fit feels for both the bootcamper and for Buffer.

As my bootcamp came to a close last fall, things weren’t a perfect fit. I began September 2015 as a content crafter at Buffer. By October 2015, we’d parted ways.

As far as I could see, I had two options:

  1. Try to find a traditional job again. I had left my old job to jump into bootcamp, but I could try to find a new one.
  2. Make my own dream job. I could try to design (and get the funds to support) the job I wanted all along.

I chose the second option. And it worked!

I launched an agency that made $300,000 in six months. I published a book. And I’m happier than I could have imagined.

I believe “failing” Buffer’s bootcamp was the best thing that could have happened for Buffer and for me.


Here’s the story of how it happened.

What it was like to start Buffer’s bootcamp


For a long time, I’d thought of being a Buffer content crafter as the dream job. Great pay. The ability to work from anywhere. Awesome retreats. Diverse staff. Heartfelt values. I think everyone who begins bootcamp agrees.

Like a lot of content marketers, I thought of Buffer as the the place to be. To me, Buffer was a special place where only the chosen few could work. It was a super loving, positive environment where you could try new things, fail big, and always be learning.

Long before I had an interview, my friends and I would fantasize about what it would be like to work with the Buffer family. Leo, Belle, Kevan, and Courtney were huge inspirations to me as a blogger. (And they still are.)

Needless to say, when I got the invitation to begin bootcamp, I said yes.

Of course, that came with a risk. I’d leave my full-time employer, whom I really liked. If it didn’t work out, I might be on the job hunt again in six weeks… and I live in a town where there aren’t a lot of jobs, so that would probably involve a big move.

But when you have a shot at working at Buffer, you take it, right?

Well, I did. I jumped in.

And I landed like a hedgehog in a bucket full of water balloons.

(OK, it wasn’t that bad, but it’s a word picture I’ve been wanting to use for a while.)

What it was like to fail bootcamp

It was sad, but in hindsight, unsurprising.

I’m not a good fit for Buffer. I’m too aggressive. I’m too confident in my opinions. I’m too competitive (Competition is the #4 value in my Gallup StrengthsFinder).

As the mismatch became more and more apparent, Buffer and I parted ways at the conclusion of my bootcamp.

I ended up sending the team these lines in an email:

Over the past week, my buddies and I have been talking about wholeness—specifically whether Buffer is the best place for me to be wholly me. Right now, we don’t think so. =)

^ I mean that smiley, too.

Although it’s tough to say goodbye, I’m sure that this is the wisest option for me. I’m so very, very grateful for the opportunity to work alongside the World’s Best Humans (which is the nickname I’ve given you when talking to my non-Buffer friends). I’ve learned a great deal, and I’ll probably look back at this brief, 5-week season as a turning point in my life for the better.

Looking back, I realize that if these things didn’t come up during bootcamp, they would have come up later—and that would have been harder on everyone.

You can “fail” successfully

Turns out, what some would call a “failure” became one of the most successful changes of direction in my life.


We chase a lot of things that we think will make us successful—but won’t. For me, the Buffer bootcamp experience taught me a valuable lesson:

Failing to achieve false success isn’t really failure.

After all, if you’re striving for something that’s not really right or good for you, and you get it, did you really succeed?

For example: Let’s say you go out with someone for a few dates. You realize you’re just not into them. But you keep at the relationship, and when they ask you to marry them, you say yes. Would you call that a successful relationship? (I wouldn’t.)

Or how about another example: You’ve declared a major in astrophysics at your university. But after taking the first few weeks of classes, you realize that there’s a lot less stargazing than you thought there’d be—in fact, you find astrophysics boring. But you choose to power through the next 45 months and finish a degree you never plan to use in your career. Was that a successful use of your time in college? (I don’t think so.)

When I sent my goodbye email, Leo followed up with some kind (and true) words:

I remember something Sunil told me: […] “Being successful doesn’t always mean joining Buffer”. This is an example where I feel like you’ve been incredibly successful during the bootcamp and the outcome of not joining Buffer seems like a wonderful one.

Sunil’s a wise man. When it comes to Buffer’s bootcamp, being successful doesn’t always mean joining Buffer.

The way things played out afterward made that abundantly clear to me!

Failing gave me room to focus

When I told a few of my friends that I was no longer in bootcamp, one of them actually sighed in relief. “Now you can focus on your own thing.”

Laura Kranz, my wife and business partner, and I had been side-hustling a content marketing agency for almost a year. It was fun, and we were beginning to pick up some momentum.

Laura was already spending a good deal of time setting up the business to grow. In fact, right before I started bootcamp, we picked up a client that allowed us to bring on our first team member.

While Laura and Jayson were hard-charging at our business, I was working Buffer by day and Overthink Group by early morning and night.

To be honest, neither Laura nor I anticipated Overthink’s success happening so rapidly. It snuck up on us.

And that meant that with Buffer off the table, I had the two options I described earlier:

  • Try to find another traditional job. I could let Overthink Group simmer on the side a little longer until I was sure it was stable enough to focus on full-time.
  • Make my own dream job. I could pour my energy into making Overthink Group stable and growing now.

I chose the second option, and boy am I glad I did.

When I focused on one thing, it took off.


I took a bet that we could turn a tiny company making just enough to cover our rent into a company that gave us all the benefits that had drawn me to Buffer:

  • Working wherever we want
  • Working whenever we want
  • Working with the kind of people we want to work with
  • Learning and growing in an upbeat environment
  • Making the kind of money we want

All of this wasn’t going to happen on the side. Failing bootcamp gave me the time and space to build my own dream job, and dream jobs for those around me.

A ‘dream job’ isn’t the only path to happiness: 4 life lessons from my experience

I went into bootcamp with a mix of joy and anxiety. There was a pragmatic anxiety: What if I ended up on the job hunt again in six weeks? Then there’s the interpersonal anxiety: What if the people I had looked up to for so long didn’t think I was good enough?

I think these are understandable concerns. But here’s what I learned.

1. If you don’t finish bootcamp, the Buffer team won’t stop loving you.

By the time you’ve made it into bootcamp, Buffer’s not asking, “Are you good enough?” They’re asking, “Is this person right for Buffer?”

And if you don’t make it, you’ll still have friends there. I still keep in touch with a handful of awesome Bufferoos.

When someone leaves, there’s not a feeling of people turning on that person. I saw ex-campers referred to in HipChat as good friends.

2. If you don’t finish bootcamp, it doesn’t necessarily mean you did poor work.

I was told I did great work while I was there—some of the best blog posts I’ve ever written went live after I left!

And that’s not just my story. Others have done fantastic work and not completed bootcamp. Like I mentioned earlier, bootcamp is much more about the two parties seeing if they like working together than it is about vetting your professional skills.

Bottom line: that Buffer value of positivity? It applies to how the team talks about you, even if you didn’t turn out to be a good fit for the culture.

3. Buffer’s values are great. Mine are, too.

Being a positive, transparent no-ego doer doesn’t make you a fit for Buffer’s culture. In reality, that’s just a prerequisite.

I hold to Buffer’s values. They’re what drew me to Buffer. But I wasn’t the right fit. I know a lot of people who share Buffer’s values who wouldn’t fit either.

I found this both scary and comforting.

It’s scary for a really obvious reason: you could fully believe you’re a great fit because you share Buffer’s values, and you could be totally off base.

But it’s comforting, too: because Buffer shouldn’t be your litmus test for what your values are. Your values are yours—whether or not you get a job offer from Buffer.

4. Buffer isn’t your only path to a fulfilling job.

Sometimes it feels like everyone wants to work at Buffer. Sometimes it feels like every workplace wants to be more like Buffer!

I can understand why. The Buffer team has makes a good product, hires good people, pays good money, and has good times.

But Buffer isn’t the only place you can have that ultimate dream job experience.

Don’t get me wrong: Buffer’s a great place to work. But it isn’t the ONE SHOT you get at having the life you want.

You can find other like-minded companies. (There are others!)

You can negotiate for the benefits you want from more traditional employers.

You can even start your own business and give yourself a dream job—like I did!

It could be the beginning of something even better.

A few more thoughts (mostly yours, I hope!)

Well, I’ve spilled my guts. ;-)

If you’d like to know more about what it’s like to run your own agency, you can read more of my story at

If you have a “failed successfully” story like mine, I’d love to hear yours. Leave me a comment, or tweet me!

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