An Actual Correspondence With A Reader Whose Startup Failed and Who Is Struggling to Quantify His Accomplishments
In a previous blog post listing eight reasons I didn’t call you for a job interview, I wrote why it is necessary to quantify, not just describe, your achievements in your resume.
I received the following email from a reader asking how exactly he can do that when his last company imploded and he’s embarrassed about his career:
Hi Anastasia,
I just read your website article on '8 Reasons I Didn't Call you for An Interview'.
I found the post really helpful, particularly because you were extremely direct in the advice you provided. Thank you for that.
I wanted to ask for your help on something. You mentioned the importance of providing quantifiable results (e.g. sales quota, revenue etc).
My problem is I have been part of a failed startup that had poor results - not due to my lack of skills but a mixture of difficult market conditions that meant we couldn't grow fast enough to reach profitability. I am in a situation now where I feel ashamed to even put any figures on my resume. Do you have any suggestions on how to position a resume with this type of problem?
I am 34, not far into my career but I feel like my credibility is damaged because of the failure. I've applied to about 100 jobs but have had 0 interviews.
Thanks,
Gary
What a great question, and a common challenge that many of us face in our careers.
NOBODY’S CAREER IS FREE OF FAILURES AND SETBACKS. NOBODY’S.
To pretend otherwise is to deny reality.
And yet, we persist in beating ourselves up and hiding our failures and setbacks instead of using them as interview ammo and openly boasting about 1) what we tried, 2) how we failed, and 3) what we learned.
[TL:DR]
If you want to skip right to the solution, scroll to the bottom.
But, you’ll miss the most important part, which is shifting your perspective toward seeing failure as valuable, without which your solution isn’t going to be as convincing to hiring managers.
So, please don’t skip to the bottom.
I was so touched by the honesty and courage in Gary’s email that, even though I was running late for boxing practice, I recorded an answer on the fly while my response was still raw and fresh:
It’ is easier to convince ourselves that failure is the universe telling us to stop doing something, than it is to persist through disappointment. We accept it as a referendum on our talents and skills. We take it personally, forgetting that failure is a necessary and intrinsic component of accomplishment. We cannot do without it.
Failure serves us in two ways:
It imparts invaluable lessons that, when examined and reapplied, build our mastery in a given business context, professional challenge, or personal pursuit.
Failure builds grit.
Let’s say some more about the latter. Grit is variously defined as:
“firmness of mind or spirit”
“unyielding courage in the face of hardship or danger”
“courage and resolve”
“strength of character”
“I never lose. Either I win, or I learn.”
Multi-title UFC champion Conor McGregor, who famously lost to American boxer Floyd Mayweather.
Grit is also the #1 professional trait that leaders obsessively cultivate and that hiring managers screen for in job applicants.
Because grit is quite literally a determinant of success.
Here are some examples of famous entrepreneurs who failed before they succeeded, demonstrating a great deal of grit and perseverance in the face of catastrophic failure:
James Dyson built over 5,000 failed vacuum prototypes before developing the ones that earned him millions.
Colonel Harland Sanders’ chicken recipe was rejected 1,000+ times before a restauranteur finally accepted it. He was in his 60s when he founded KFC.
Twitter cofounder Evan Williams first launched a podcasting platform called Odeo, which quickly went under after Apple announced that the iTunes store would include podcasting.
Henry Ford built two failed car companies that left him broke before he founded Ford Motors.
Mark Cuban’s resume of failures includes failing as a carpenter, as a cook, and as a waiter (for not being able to open a bottle of wine) before selling Yahoo for billions. He reminds us: “I’ve learned that it doesn’t matter how many times you failed. You only have to be right once.”
Soichiro Honda was turned down for an engineering job at Toyota. LOL.
Thomas Edison holds over 1,000 U.S. patents. His grade school teacher told him he was too stupid to learn and suggested a career that did not depend on intellectual faculties. His teacher might have been proven correct if Edison had quit after 8,999 failed light bulb experiments. Luckily, Edison’s 9,000th attempt was successful.
Walt Disney got fired for lacking imagination and original ideas. After all, his first animation company went bankrupt! Even after experiencing mild success, he still got turned down hundreds of times when raising money for Disney World.
Steven Spielberg was rejected from film school three times.
Tim Ferriss’ bestselling 4 Hour Workweek was turned down 25 times.
Oprah Winfrey was got fired from her job as a news reporter in Baltimore.
And perhaps most famously, Steve Jobs got fired from Apple.
Business literature abounds with stories of failed enterprise. Because failure is a certainty.
Do you think any of these people are embarrassed by their failures, or wear them as a sad badge of incompetence and disgrace? No! Their stories of resilience are our how-to guide when our best laid plans unravel. You’re meant to stop, examine, apply the learning, and attempt again.
You’re not meant to quit. You’re NEVER meant to quit.
But I promised you solutions on how to message failure in your resume, not just pump you up with my ra-ra enthusiasm. I shall deliver!
When I returned from boxing practice, I continued my correspondence with Gary, which is reposted here below with his permission, along with my advice:
Hi Gary -
Thank you for your thoughtful email. I was very touched to read it because it comes from a place of real pain and confusion, and I'm grateful to you for trusting me with it.
This is an excellent question. It's so awesome, in fact, that I had to respond to it right away, even though I was running late for my boxing coach. I recorded a quick video response before running out the door -- my first one ever, since I have been meaning to start a YouTube channel but hadn't prioritized it until now -- just to get my answer to you while it was still fresh.
This response is here and it is currently set to private.
With your permission, I'd like to make it public and share it, as I think many, many, many people would find it helpful.
I will very likely write a more detailed blog post about this. But in the meantime, I desperately want to get you the narrative help you need to reposition your resume and your entire message. You're looking at the whole thing the wrong way.
Let me first admit to you that I, too, have my own failed startup story. It was a tech company in East Africa that did not do as well as we had hoped. Our projections proved too optimistic for a very tough market, and we could never get the transaction volume up to where it made sense to keep taking investment. After licking my wounds and checking my ego, I turned this experience into a goldmine of interview material and quantifiable learnings snatched from the jaws of failure. It's so, so, good. It's the stuff that business leaders and smart companies obsess over, and the stuff that gets entrepreneurs paid million-dollar advances to write about.
You, too, are sitting on a gold mine. It's all in the way you position it, and what message you'd like to convey to your prospective employers. I haven't seen your cover letters, but I bet there isn't a very compelling story there, and I bet your resume doesn't back you up, either. Because you're trying to hide and sideline what should actually the main event in your application.
Please view my video response and let me know if I can help clarify any further. There's actually much more to say on this topic, but I'll give you space to process my response and ask a follow-up question first.
How can I help you get beyond this? Would you want to potentially work with me on developing your narrative, your strategy, and your application materials? Would you like to jump on a 20-minute call just so I can understand your particular challenge and you can ask me anything you want? How can I help?
And of course, please consider granting me permission to make that video public. Lots of people are in your shoes. Thank you for inspiring me to take action on this question. You really impacted my day.
All the best,
Anastasia
—
Hi Anastasia,
Thank you so much for responding so quickly and for using my question for a video response.
I am absolutely fine with you publishing that and I sincerely appreciate it.
Honestly, you are the first person on the planet who I've actually plucked up the courage to ask for advice on this. Crazy as we've never spoken but your blog piece was the most useful piece of information I've read in about 4 months of job discovery.
I've had dozens of discussions with resume reviewers but even felt too ashamed to raise this and instead just try to figure it out alone. It's kind of childish of me and I have no idea why (well I do, it's because I'm full of pride/ego).
Thank you for sharing your story with me about your tech background in Africa. It is good to know you were able to find and harness success from it.
Based on your response, I need to cycle back and rethink my strategy - is it ok if I contact you again in a few days to let you know about the 20 min call? I am based in London so hopefully that's ok.
Thank you again for all your help and kind responses so far Anastasia.
Gary
—
Hi Gary -
Practice a little gratitude this afternoon for finally finding the courage to ask for advice about it. Everything in due course. Maybe if you had asked earlier, your mind would not have been ready to receive counsel, and the effort might have been wasted. Maybe you would have gone to an individual with whom you did not connect intellectually, and the message would not have resonated. We'll never know. The point is, however, that when you finally did, you got some useful answers, so you did everything right and exactly at the right time.
People are so very different. For me, our challenges in East Africa never appeared as a referendum on my worth or skills as a professional, even though my experience of those challenges was of course deeply personal. In part, maybe this is because I did lots of mindset preparation while serving as a founder and a leader of a startup, and so I knew it was going to be hard, most likely to fail, and that even if all was lost, I'd at least be able to scavenge the learnings. I was always very attentive and on the lookout for anything I could take away from what didn't work. In fact, failure is consistent with the pareto principle. Faaaar fewer companies will fail than succeed, so I'm in the majority. But now I want to move myself into the impressive 20% minority. How do I do that? By ensuring I learn from failure and teach others. Very few entrepreneurs do that work, because they're too ashamed, so they'll stay in the 80%.
I don't know you but perhaps you didn't spend enough time immersing yourself into the all-too-common struggles of an entrepreneur, and so this really felt raw for you.
That's good though, because the more raw your feelings, the more keenly you'll be able to remember what happened and excavate your experience for the delectable business insights hidden in it. Welcome to the 20%.
Here are some questions to help you begin examining and quantifying failure:
- How large was your total addressable market, and how big of a problem were you trying to solve? Why'd you want to solve it?
- What was the hardest thing you did at that job, that required the most effort? What did you do?
- Now that you're such an expert on this particular industry, what's the biggest thing you might advise another company trying to do a similar thing?
- Do you recall any little wins?
- Those days when it felt like it was working -- what was going at the time and why did those things feel like victories?
- What did you and your coworkers overlook that now, with the benefit of hindsight becomes clear? This could be anything from market conditions, to organizational culture, to hiring better, to doing more price testing. Anything.
- What's the coolest thing you learned?
- What are you more informed or experienced about now?
Take all the time you need, and reach out when you need to.
And good luck. Remember, this whole thing is a matter of your skewed perspective. From my point of view, I'd like to learn from you because you have valuable stuff in your head that could help me and others. But for you, the same set of variables constitutes failure. Rearrange your perspective.
Best,
Ana
P.S. Regarding mindset, it's really powerful stuff. The brain needs a warmup to do this hard work, just like you might warm up before a hardcore workout. I cannot recommend the audiobook The Obstacle Is The Way highly enough. I recommend it to all my clients who feel like everything is completely screwed and they don't know where else to turn. I think it will change how you see things. It's stoic philosophy, but in digestible, motivating, actionable form.
The How-To You Wanted to Skip to Is Here!
Notice that in my emails with Gary, I haven’t given him the exact formula for how to message failure in the resume. That would be skipping a few important steps. There really is no such thing as The One True Failure Narrative; failure is individualistic and lessons are specific to circumstance. That’s why they’re so valuable in business!
So to help Gary develop a compelling resume, we first need Gary to shift his mindset and examine his experience for learnings. After that, writing the resume becomes a walk in the park.
To develop a compelling failure narrative, we must ask and answer some questions about what led to failure, such as the ones I ask above: brutally honest questions and elaborate, thoughtful answers. In those very answers, we are very likely to find a compelling story for the cover letter and LinkedIn introductory messages that we can write to hiring managers.
But first, develop your answers. And to develop your answers, change your mindset. These two are prerequisites to messaging failure in your cover letters, emails, and elevator pitches.
In the resume, it’s even more simple. For smaller companies or startups no one has heard of (such as failed ones), I suggest adding a short blurb under the position and company name describing what the company did, and that it is no longer operating. In the bullet points, describe your attempts to solve business problem x by doing y, despite the challenging conditions of z. Since you have already explained that the company did not do well, the recruiter or hiring manager expects to read about what you learned, not how you succeeded.
Examples:
Converted 8% of $1.2m market with high-touch sales cultivation despite product pricing mismatch
Business problem x: convert customers in $1.2m market
Thing you did y: provided high-touch sales cultivation
Challenging conditions z: product-price mismatch
Saved $800k in overhead costs by reducing dependence on vendors
Business problem x: over-dependence on vendors
Thing you did y: replaced expensive vendors
Challenging conditions z: high business overhead
I haven’t followed up with Gary since I sent the above email, but I’ll check in after a few days. In the meantime, if you’re still struggling to see the immense professional value in your own failure story, I’ll leave you with this passage from the excellent Pound The Stone: 7 Lessons To Develop Grit On The Path To Mastery:
“Even though we have an obsession with naturals in our society, those people always end up worse off in the long run if they never learn to develop grit. We get distracted and enamored by people who seem to have the “It Factor” instead of putting in the dirty hard work of what really determines whether you fulfill your potential in life. Grit. The only way you can really develop it is by experiencing failures and setbacks. The person who has mastered his craft has failed many more times than the beginner has even tried. The path to mastery will never be easy or without repeated setbacks and failures.”