Failing Successfully: Turning Holiday Pressure Into Progress

The holidays are supposed to feel merry and bright… but in the MSP and technology world they can create a pressure cooker of ticket spikes, staff shortages, outages, and client expectations that grow louder by the day. And suddenly, you’re looking at your own operations wondering:

“Am I failing?”

If that’s you this season, you’re in very good company, and not just within the channel.

Before we dive in, here is what you can expect in this blog:

• Why the most successful people in history were also the biggest “failures”

• Why MSPs feel like they are failing during the holidays

• How to reframe the stress and spot opportunities inside the chaos

• Five practical ways to fail successfully and shift into an “I have this” mindset

• Encouragement for leaders who feel stretched thin

• A resource to help your team steady support during December
  
  

Now, let’s get into it.

The most successful people in the world are also the biggest “failures,” at least on paper.

• Walt Disney was fired from his dream animation job because they said he lacked creativity.

• Michael Jordan was cut from his high school basketball team because he “wasn’t good enough.”

• J.K. Rowling was rejected by 12 publishers before Harry Potter sold 500 million copies.

• Soichiro Honda once said, “Success is 99% failure.”

Failure is not the opposite of success.
Failure is part of the process of success.

And in the IT world, where the stakes are high and the pressure multiplies during the holidays, that truth matters more than ever.

Why MSPs Feel Like They Are Failing During the Holidays

The pressure in December is different. It comes from all sides at once, and even the most well run teams feel it. If any of these sound familiar, you are not alone.

1. Ticket queues that won’t stop growing

You clear 15, 20, 40 tickets… and wake up to double by morning. It is not because you are failing. It is because support organizations across the IT industry routinely experience noticeable seasonal spikes in ticket volume during periods of high customer activity and reduced internal staffing. Holiday periods are consistently reported as some of the most demanding times for support teams, leading to increased workload and operational strain.

Mindset shift:
You are not behind. The season is just ahead.

2. Feeling guilty about delayed responses

With staff taking PTO, clients running year-end projects, and outages hitting at the worst times, response times slip and internal shame creeps in.

Mindset shift:
Instead of “We’re slow,” tell your team:
“We’re prioritizing intelligently. We’re communicating clearly. We’re solving what matters.” 

Perfection isn’t the goal. Stability is.

3. Clients expecting 24×7 magic from a human-sized team

Holiday pressure makes every missed call or after-hours ticket feel like a failure. But your value isn’t in doing everything alone — it’s in creating a system where clients always feel supported, no matter the hour.

Mindset shift:
Scaling support is a strength, not a sign of weakness.
Delegation, overflow partners, and backup coverage are strategic moves of a healthy MSP, not a failing one.

4. Processes that suddenly seem inadequate

Handoffs break. Documentation gaps appear. A forgotten escalation pathway shows its teeth. The holidays don’t create weaknesses, they reveal them.

Mindset shift:
This isn’t failure.
This is real-time, high-value feedback on what to strengthen for Q1. Seasonal stress reveals the exact areas that lead to long term operational maturity.

How to Fail Successfully

The most successful people in the world do not avoid failure. They recognize it, learn from it, and refuse to let it derail their momentum. MSP leaders can do the same, especially during the most demanding time of the year.

1. Expect the surge, don’t fear it

When you know holiday chaos is normal, you stop taking it personally. Preparation = power. Normalize the idea that December is not business as usual.

2. Break the shame cycle

Teams perform better when they’re encouraged, not corrected into confidence.
Small wins matter. Celebrate the resolved tickets, the calm escalations and the clear communication.

3. Reduce what you carry by reducing what you handle

Great leaders don’t carry stress alone.
If after hours coverage is draining your team or if the ticket queue is stretching beyond capacity, bringing in outside support is not an admission of defeat. It is a sign of operational maturity and foresight.

4. Reframe setbacks as data

Every missed step, delayed reply, frustrated client, or broken workflow that surfaces in December is information.

This is the season that reveals what is working and what needs refinement.

Reframe the frustration.
This is insight pointing you toward your next level of growth.
All of it is information, not indictment.

5. Measure yourself by your consistency, not by the hardest week

No single moment defines your worth.
No single outage defines your quality.
No single tough client defines your success.
Your track record speaks louder than your toughest season.

If You Feel Like You Are Failing Right Now

You are not failing.
You are growing through the hardest part of the year in a high pressure industry. That growth does not feel smooth. It feels like strain, and that strain often feels like failure.

But when you continue to believe in your ability to push through and continue to show up despite the weight, your breakthrough is closer than you think.

You are not falling apart.
You are leveling up.

The most successful people on earth have something in common. They did not quit when they failed. They learned how to fail successfully.

Your holiday stress is not proof that you are behind.
It is proof that you are moving forward.

Your success story is being built right now, in the middle of the chaos.
And like every great story, it starts with a season where everything felt impossible… right before it wasn’t.

Turn Holiday Pressure Into Progress With Support That Never Sleeps

If your team is feeling the weight of December, you do not have to shoulder it alone.
Our Holiday Help offer provides 24x7 live technical answering and overflow support so your clients stay steady and your team can breathe again.

Explore the offer here: Holiday Help
Let us help keep your queue moving while you keep your business moving forward.

Contact Us Today