So, you’re ready to start a business, or maybe you already have, or perhaps you’re still dreaming. 

Whatever the case, I have an important question for you.

How do you decide who you let in influence the vision and direction of your company? 

I’m not just asking about ownership, but on other issues like leadership, decisions, advice, and authority, who do you allow inside?

I have found this to be a particularly tricky subject for some entrepreneurs. When you start your own business, you’re usually more than ready to get away from the bureaucracy and politicking, and it is easy to try to avoid people as much as possible. No people, no problems, right? Or maybe, being the visionary that you are, you have had a lot of trouble being understood by others, or finding the freedom to do all that you thought could and should have done.

Whatever the case, many founders start their businesses in large part for the freedom and autonomy that it offers. One definition for an entrepreneur that I quite like is someone who would prefer to work 80 hours for themselves than 40 hours for someone else.

However, freedom and autonomy, though enjoyable, is no cure-all. If you’ve started your own business, you know what I mean. There is this odd moment after you transfer out of your old role into THE role, aka the only position in the company. The moment I’m referring to is the one when you realize that you’re the one who has to do those things someone else has always done for you. Yuck.

You will continue having these mini-moments and slugging it out until you finally decide to hire some help.

Fortunately, for most founders, this is a pretty soft landing. While that first hire can hurt the bank account, it does wonders for your schedule. You get to lop off all the low hanging fruit, all the tedious, eye-gouging stuff you hate and hand it all to someone else. It’s glorious, and more often than not, this first hire can make you feel freer than ever. 

However, as the business continues to grow, eventually, each hire feels less like an asset and more like a liability. Payroll seems to be getting larger and larger. It’s scary. Your inbox gets fuller and fuller, with requests from staff who need your assistance. You are roped in constantly. You contemplate not going to the office, just to get some work done for once.

At some point, decision time comes. This business, your baby, is too big to grow alone. But who in the world will you trust to help lead what you find so precious? Who is capable enough to grow and protect your primary, if not sole income source? Who are you willing to lean on, at least to some degree? This decision is difficult at best.

What’s on the other side of the wall?

When faced with a big decision like this, I find it helpful to think of the analogy of a giant wall. When I’m on this side of the wall, all I can see is this side of the wall. I can guess what the other side of the wall is like, but I can’t see, touch, or experience it. I can even hypothesize what is on the other side of the wall, but there are only two ways to find out.

First, you can climb the wall and jump straight in. For small walls (tiny problems), it works because when you aim small, you miss small. But when your organization is big, when lots of people are counting on you, when you have too much to lose, climbing up and jumping straight in isn’t always the wisest option.

The other way to know what’s on the other side is to ask those who have been there. I’d be willing to bet that while no one has been in your exact situation, plenty of people have been in very similar situations, and they know what the other side of the wall holds. These people can help you choose whether or not you should jump.

The first step

The first person to let in is someone who has been there before, a guide who can show you the way, and lead you in to decide for yourself. This person can be a parent, a mentor, a coach, someone older than you, maybe even someone younger than you. It doesn’t matter who they are or how old they are, only that they’ve seen the other side of the wall. It is usually the easiest to invite someone who has nothing at stake. They can give you real, honest advice without trying to sway you in their direction.

If you get nothing else out of this article, get this. Don’t walk this road alone; find a guide. The right guide will save you so much trouble, heartache, and expense. This person will also help you to navigate the second step.

The second step

Invite someone else into your decision-making circle. This person is not necessarily in a leadership position in your company. It could be as simple as delegation, but take at least one thing in your inbox right now, and make someone else wholly responsible for it. I mean like even-you-go-to-them-for-a-decision responsible for it. Completely 100% their responsibility. I’m not going to lie; this is difficult, but let me speak from the other side of the wall. 


Just wait until the first time someone else comes to you with a question on that issue, and you get to say, “I don’t know, ask so-and-so.” It is one of the most liberating experiences. Suddenly, for the first time in a really, really long time, you don’t have to know everything. You aren’t responsible for everything. There is once again a little light at the end of the freedom and autonomy tunnel. Surprisingly, it’ll be where you least expected it, in submitting to someone else.

The third step

Now we’re getting to the good stuff. Now that you’ve tasted what it can feel like to invite someone into real authority, it’s time to build a leadership team. Yep, we’re going for it. A strong leadership team is God’s greatest gift to leaders. There is so much strength in a team dynamic. The right team can boost your competence, capacity, creativity, and courage. This kind of team will let you accomplish more than you ever thought possible. They will challenge you for the better, and they will keep you at the absolute top of your game.

However, building this team can feel like being a teenager all over again. You feel awkward, and you accidentally step on people’s toes, you don’t quite know where you fit in, you wonder if anyone likes you. It’s the full 8th-grade experience except, fortunately, the acne is behind you this time. 

Hang in there. Lean into your guide. Seek out help. Read and learn together as a team. Over-communicate. If you want to build a great and enduring company, you need a great team of people to help you.

The fourth step

Ok, so you have a guide; you’re delegating some important decisions, and your leaning into the strength of your leadership team. 

Now, here’s the final test. Are you ready? 

Go on vacation for a month! 

Yep, one full month. 

If you can leave your team behind to manage all the decisions (even the important ones) for one whole month, and the business still moves forward, then congratulations! You did it! You have finally found the freedom and autonomy you’ve been wanting. Go, turn your phone off, disable your email, and enjoy it because you’ve earned it!

Here’s the best part. A team that can work independently with a founder who is confident in their abilities will thrive like never before. There are very few things in life that make you feel more confident and self-assured than someone else’s well-founded trust in you! Trusting and relying on your team this way is what is best for you, for them, AND it is what’s ultimately best for your company.