Listen instead on your Monday Morning Drive:

I studied martial arts for many years. I learned multiple disciplines, earned various black belts, and instructed newcomers. In martial arts, particularly when working with teenagers, we often discuss “punching above your weight.”

In training, we learn by sparring with people more skilled than we are. Conversely, when you’re more experienced than the person you’re training, you don’t try to prove it to them — you simply keep them challenged. As they improve, you use better techniques to teach them to develop proper form.

Businesses “punch above their weight,” too. A client of mine from years ago built his business on punching above his weight, which helped him win major, high-profile projects that could have gone to companies with more experience, longer market presence, and stronger brand recognition. His scrappy little company kept punching above its weight and winning jobs.

But punching above your weight doesn’t always work. Sometimes, you get in over your head.

When You’re Outmatched

Recently, someone asked me about a job they were trying to win. After they described it, I said, “You’re punching above your weight.”

They replied, “We have to punch above our weight to grow.”

There’s some truth to that. But let’s consider a few scenarios.

Let’s say the job you’re pursuing is smarter than your best person. If your best employee (or your top three people together!) struggles to execute it, it’s not the right job for you.

You may still pursue the job with good intentions. You’ll see the extra zeros in the revenue numbers and think, “This will double our year. We’ll get better at it next time.”

But do you know how far up you’re punching? You can’t see the level you’re competing at. You don’t know how good the competition is. And you may get beat up — not by someone who will teach you, but by someone who will smack you down to make a point.

The Ego Factor

Ego also drives people to punch above their weight.

They want the revenue, the glory of doing a big job, the social media bragging rights. These are the situations I worry about most: when we don’t know what talents and skills it’ll take to succeed, whether we have them, or where to find them.

“We’ll figure it out later” is a dangerous mindset.

So is “Other people did this, so I can, too.”

When It Works

I once worked with some very smart, talented people in a startup that punched above its weight. I was brought on because of my talent, and my colleagues and I solved problems together.

No single person made everything work. We had one person very good at applying technology, another person skilled at logistics and planning, and another good at testing. Executing complex projects required collaboration.

The exciting part? We got to do projects no one had done before, so anyone who attempted them punched above their weight.

If your company takes on big jobs that rely on a single person to figure everything out — and that person is critical for every job you do — you’ve set yourself up to fail. You can’t build expertise around one individual. A team of capable people ensures sustainable work and growth.

The Buyer’s Perspective

Buyers know when you’re punching above your weight. They hear it in your voice, see it in your proposals, and recognize from your website and marketing that a project might be out of your league.

But that doesn’t mean they won’t give you a chance.

I got my first big job for a major agency client because, while the agency recognized we might be punching above our weight, they thought we could handle it. The job wasn’t technically complex, but it was a large, high-profile event in a non-standard venue — a dusty, old exhibit hall.

The agency needed a good partner and took a chance on a local company. Sometimes, buyers let you punch above your weight because you offer good value, represent a financial risk they’re willing to take, or because they trust you.

The client told me they were considering another company but felt that company misled them about their capabilities. Meanwhile, I was clear about our potential shortcomings and areas where we had less experience, which wasn’t concerning to them — their team was strong in those areas.

It’s the companies that aren’t clear about their shortcomings upfront that make me nervous — companies that punch above their weight while customers believe they’re hiring someone playing at the right level.

I’ve seen these situations fail dramatically.

How to Punch Above Your Weight Successfully

When you do punch above your weight — and you will — keep these best practices in mind:

1. Hire Better Freelancers

There are great staff technicians out there. But at a certain level, they won’t improve significantly. The number of jobs they do is limited, and they always use your gear.

Freelancers have more experience and know more best practices. Your team won’t get better by working inside your bubble, but freelancers constantly improve by working outside of it. They bring broader experience to the table.

Find the best freelancers you can. Pay them extra for pre-production time because you need to pick their brains — whatever makes the job worth their while.

That’s how you improve. Next time, you won’t be punching above your weight.

2. Skip the Shortcuts

If you see a shortcut, don’t take it — it may be a trap. Cutting corners may lead to your downfall.

Attempts to save money when punching above your weight will come back to bite you. You’ll pay for this experience with lower margins. The revenue will look good on your P&L, but you won’t generate your usual gross profit.

Don’t worry about saving money. Do everything you can to make the job go well, regardless of the cost. Experience will help you make more money next time.

3. Live Your Core Values

Don’t let your core values slide. Make them visible — paste them on your wall or hang them on your monitor — because they’ll be challenged while you punch above your weight.

Your core values aren’t “make money at any cost.” They’re “take care of your customers,” “take care of your people,” and “do good work.” Always err on the side of your values.

The client I mentioned at the beginning of this blog post who punched above his weight occasionally lost money on shows. He thought he was protecting his core values, but to avoid financial losses, he needed fiscal responsibility to be among those values. He would do a great show and the client would be happy, but the supplier would lose money.

Core values matter. Finding the right way to do a job at the best cost matters more than pursuing perfection regardless of expense. Take care of your customer, the show, and your people.

Approach With Caution

If you think it’s time to punch above your weight, be cautious. Remember your core values, avoid shortcuts, and hire people better than yourself.

Let common sense lead instead of ego, and eventually, that challenging job may become your average job.

If you’re seeking empty revenue, big numbers to massage your ego, or a huge job you’ll flaunt online to attract other customers, you’re missing the point. Attract the right customers first and do the work you’re good at. Let someone else chase shiny objects and neglect their customers — so you can win those customers over.