If you’ve been around the corporate world long enough, you might remember when “failing up” was the latest concept in corporate success. It describes the ability to rise above failure and move on, to share your experiences with others, understanding the point of failure, learning from it and moving on.
Like most corporate cliches, it came and went. Fortunately, it never became an acronym. But “failing up” came back to my mind recently involving a side business that a close friend and I invested in a year ago. (No, it is not my email agency!)
This month, we shuttered that business. It failed for many reasons. The entire experience was, well, an experience. We both learned a lot, but it didn’t help us keep the doors open. Now, we’re closing this chapter and moving on.
Although this business failure happened apart from my work in email, it also brings me back to what I’ve learned over 27 years of working in all aspects of our industry, from being a newcomer in digital marketing to leading an email agency today, surrounded by amazing people and doing work that helps companies achieve their goals.
When failure is an option
This whole experience of trying something new and having it fall flat is like so much of what happens in our work as marketers. We feel defeated when it seems we can’t get a leg up on our challenges. We stick with easy, safe projects instead of risking the unknown to try new things.
That’s the wrong approach. Risk is part of life. You have to take risks regularly to keep learning, push the boundaries of what you know, test what you don’t know and grow as a result.
Now that we’re knee-deep in 2025 and trying to navigate another year and challenges ranging from the mundane to the insane, avoiding risk seems more attractive than ever. But that opens us up to another risk — stagnating or even falling farther behind because of our fear of failure.
Let’s think instead about failure as something we have to accomplish and not avoid. Here are three ways to approach failure. Each one reminds us that failing can make us stronger, better and smarter.
1. Testing
When our agency talks with potential and new clients and we bring up the subject of testing, we often hear the same thing over and over:
“We tested that once and it didn’t work.”
Oh, man. If I gave up every time an email test didn’t work, I’d be unemployed permanently.
Here’s the thing about testing: Tests are designed to fail sometimes — to help you discover what works and what doesn’t. The hypothesis you’re trying to prove is either “yes” or “no.” When you run a test and it appears to fail, the failure isn’t isolated to that one test.
If a test fails, run it again. Try to see if you can replicate the failure. This ensures that your result isn’t a fluke. Then evolve it based on what you learned.
When you set up a test, you must incorporate the failures and successes to ensure your results are valid. Testing just once isn’t enough.
But that’s one reason people shy away from testing: They don’t want to fail. It might not be just their own fear of failure. Maybe the boss doesn’t like failure, either, and one failed test could mean the end of trying new things.
Whatever the reason, we hesitate to invest time, energy and souls in something new because we think we’ve wasted all those resources. But if we’re good marketers, those failures can teach us the direction we need to follow, to a destination we never could have reached if we didn’t risk everything, including failure and try.
Yes, testing has many downsides. But it has twice as many upsides. When I talk about testing, I’m not saying you should limit yourself to testing easy things like the subject line. Your subject line is just one component of your email message, and your message is one component of your campaign.
Embrace your testing failures along with your winners. Every test I’ve done has had many failures, but I learned from them and made them into successes.
Dig deeper: Why testing is a marketer’s most powerful tool
2. Change
Organizational change is a risk, whether it means a shakeup in team structure and management or the introduction of new technology and processes that disrupt the established flow of business.
We see this every day in our agency because we help companies manage the migration process from one ESP to another. These moves are already risky for companies because they involve key business platforms. The more we depend on data, the more entangled our systems become because they work across different systems, vendors, processes and queries.
A platform migration is a risk. Big change inside an organization is a risk to your job, revenue and organizational stability. But change has to be part of your business regimen. You can’t avoid change and its accompanying chance of failure because when you do, you become stale. You’re stuck in the quagmire of past practices.
As I mentioned above, testing is entrenched in the need for change. Change can bring failure, but you’re doing it for the potential of large success. You can mitigate the chance of failure by thinking through the process like a chess master, evaluating each move, anticipating what could go wrong, and developing plans to mitigate or protect yourself from that failure.
You can bring people in to help you manage that change, to create an atmosphere of team effort and group consensus and buy-in and manage up.
Yes, you could fail. But then you get up and assess what you learned, make changes and try it again now that you’re smarter.
Dig deeper: How to survive (and learn from) email marketing mistakes
3. Career
Over the years, I’ve left jobs, lost jobs and even been downsized. Sometimes, it was out of my control. Other times, I was not smart about office politics. Whenever I left a company or got let go, I seriously reflected on why it happened. What was my fault? What could I have done differently?
It’s easy to blame the company when they show us the door. Sometimes, it’s the company’s fault, and sometimes, it’s ours.
Sometimes, failure is an option, and it happens in every part of our lives. Careers are no different. Some people move from one company to another and make the same mistakes over and over because they didn’t take the time to understand the control they have in changing those outcomes.
Don’t let fear of failure dominate your career path. Build on it with every experience. If you’re in a position where you don’t feel appreciated or fulfilled, if slogging through the day makes you miserable, then look for change. But take ownership of your role in it.
Dig deeper: The surprising truth about how to achieve your marketing goals
Wrapping up
Yes, losing a business is devastating, even if it’s a side hustle you take on in your off hours to help you save up for a comfortable retirement. When our business closed, I had to say goodbye to some talented people. I wish we could have found another way to solve the problems, but failure is a cold, hard fact of business. Sometimes, things just don’t work out.
I learned a lot from this failure through self-reflection, which I didn’t do earlier when I was younger and dumber. But along the way, as I gained experience, I learned that you have to look inward, whether you’re doing A/B split or multivariate testing on an email campaign, adding new technology, replacing systems or moving from one job to another. That self-reflection — and overcoming the fear of failure — can shape every aspect of your experience.
If you know things need to change, whether you must prove to your boss that a new initiative will pay off or find a new job, you face the risk of failing. But don’t let that stop you from trying something new. Be smart. Plan your moves. Create a contingency plan if something fails. Look for lessons from both your successes and failures.
I remember an incident from my work for an ESP when I messed up so big it got my CEO’s attention. He called me on the carpet about it.
“That was a big mistake,” he said. I thought his next words would be, “You’re outta here, pal!” Instead, he said, “What did you learn?”
I told him. He replied, “I don’t care that you failed. Just don’t do it again.” And I never did.
Anybody want a cup of coffee?
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