Are you standing in the way of your business strategy?

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It’s extremely common for construction executives and business owners to struggle with impostor syndrome. 

I work with dozens of Top Contractors around the country, and as we build their strategic business plans, even the most seemingly confident people doubt themselves—and in the worst cases, it genuinely impacts their strategy. 

In the absence of confidence, they dream small. In the absence of confidence, they doubt their ability. In the absence of confidence, they adjust (down) their goals. They usually doubt their teams, too. 

It can be a serious roadblock to strategic success. 

But over and over again, I’ve seen executives and business owners overcome their impostor syndrome and stop holding their business back in the process. Three strategies seem to work especially well, which I’d like to share with you today. Let’s jump in. 

Strategy #1: Dream big, and dream long 

In his hallmark book, Good to Great, Jim Collins explains that the best businesses of the 20th century have a significant attribute in common: they set HUGE strategic goals for 10-25+ years into the future. Goals so big and scary that they seem wildly unrealistic (aptly called Big Hairy Audacious Goals, or BHAG). 

The truly remarkable thing about each company’s BHAG, though, was not that the business was bold enough to set it, but that they often achieve it. Having that gigantic goal tested their assumptions about what they were capable of, and inspired the owners, executives, and individual employees to produce outsized results.  

In our experience with Contractors around the country, whom we have helped reach some crazy (and amazing) strategic goals, we couldn’t agree more.  As an owner or top executive, whatever you see as possible for your business will largely determine how far your company can go. Therefore, your vision should be bold, especially the longer your planning horizon. And it is helpful to dream long (i.e. 10-25+ years in the future) because you can accomplish so much in that timeframe.   

As you dream big and dream long, you will start to test your capabilities. The more you test your capabilities, the more you start to believe you are capable of more than you ever realized.  

There is no room for timidness in the great game of business, and this kind of dreaming is great for combating impostor syndrome. 

Strategy #2: Separate dreaming and operationalizing 

If you’re like most people, you’ve probably allowed yourself to dream big before. You may have even done it by accident while doing the dishes, walking the dog, or taking a shower. 

“Gosh dang, it would be amazing to hit $100M by 2028. I want that.” 

But again, if you are like most people, you probably follow up that thought with: 

“But how will we ever do that? We need more people, more processes, more training, and more of everything before we could ever get close to hitting $100M!” 

Then, the big dream becomes more stressful than it is exciting, and subconsciously you bury the thought deep down, and prepare mentally to go back into work the next day and keep your head down. No big dream worth chasing, because it simply doesn’t seem possible. This is very normal.  

But fighting this stress is exactly what separates big and small dreamers. So, to fight it, it helps to separate dreaming and operationalizing. Instead of jumping right into how your business will get it done, take a little more time to dream. 

• Ask yourself: If we were 25 years in the future, what things would need to be true about our business to feel like we were wildly successful? 

Starting with financial goals is useful, then consider what else would make the future great and exciting (people goals, real estate ownership, investments, equipment, etc.). And don’t worry for a second (yet) about how you will do it. Just figure out exactly what would make you feel amazing about the future. The how will come later. 

If your vision doesn't scare you, then go further. 

Strategy #3: Involve your team (and anyone else who will listen) 

Now that you’ve allowed yourself to dream long into the future and started to define future success, you can start to get into the how. The best owners and executives know that they do not have to accomplish these big dreams by themselves—and in fact, they know the opposite is true: they cannot do it alone. They need their team to turn the dream into reality. 

So, what do they do? 

They write their vision down and then bring their executive team together to share it with them. They focus on all the amazing components that the rest of the team will enjoy as well. They get buy-in.  

And once the executive team is bought in, they work on getting the rest of the company bought in, their vendors, their customers, and anyone else who will listen and ultimately may be able to make an impact. 

As more people get involved, that crazy dream seems less scary. With clarity of what the dream looks like, the whole company can help bring it to reality. Then, a funny thing happens: as the team starts accomplishing milestones along the path to success, the owners and/or executives start overcoming their impostor syndrome. The “wins” prove they are capable of more than ever imagined. 

It doesn’t mean they never feel impostor syndrome again, but it usually does mean they know exactly how to overcome it. With action. 

What you should do right now 

If you are still reading and would love to beat your impostor syndrome and stop standing in the way of your business strategy, then take the following actions: 

1. Block off 4 hours in your calendar 

2. Go somewhere off-site (i.e., not in your office) 

3. Dream big and dream long (ask yourself: If we were 25 years in the future, what things would need to be true about our business to feel like we were wildly successful?) 

4. Write it down 

5. Bring your executive team together to share it and talk about how you could bring it to fruition 

6. Involve your team 

7. Celebrate wins 

8. Repeat 5-7 for the life of your business 

If it sounds simple, it’s because it is. You can beat your impostor syndrome and improve your business strategy. We know it’s true because we help construction company owners do it every single day.  

I hope it helps you, and if you ever want assistance bringing it to fruition, Well Built is just an email away. 

Spark Notes:

1. Even the most seasoned construction executives quietly struggle with impostor syndrome—and it often leads to shrinking their vision and settling for less.

2. The best way to fight that doubt? Dream boldly and dream long-term—your belief in what’s possible will define how far your company can go.

3. Don’t let the “how” derail the vision too early; separate dreaming from planning so you can get clear and excited before getting tactical.

4. Share the dream, get buy-in, and take action—because the more people involved, the less scary it gets, and the more wins you stack, the more confident you become.