Back in the spring of 2012 I was trying to answer a very important question: Would I go to graduate school and study psychology or would I become an entrepreneur?

• I had a lot of the same fears as other entrepreneurs. For example, how in the hell do you run a business?
• I wasn’t making much money with my freelance business (at the time I was writing résumés for job seekers, tutoring French, and had a couple of other odd jobs).
• I was hesitant to take the leap into entrepreneurship because it seemed so risky.

I knew I needed help, but I didn’t know who could help me.

And then I received an email that changed everything.

The email invited me to join Marie Forleo’s B-School. I watched her free video series like my life depended on it.

And when she opened the doors for B-School in 2012, I felt it was a sign that I needed to take this leap. I had exactly the amount of money in my bank account to afford the $2,000 program. I’ve never looked back.

The same thing happened a year and a half later when I felt I’d hit a rut in my business. At this point I’d applied everything I learned in B-School but had no idea how to get to the next level. Being an entrepreneur was not as fun as I’d imagined. Frankly, I felt alone, depressed, and poor.

And then I got another email that changed everything.

This time it came from Natalie MacNeil, the savvy, Emmy Award-winning redhead who runs She Takes on the World.

Natalie had also invited me to join her free training event. (And let me just say that it was clear why this woman has an Emmy Award. Her production value is off the chain.)

At the end of Natalie’s free event, she invited her viewers to apply for a year-long mastermind program called The Conquer Club.

In that moment, I knew that I needed to join.

There are logic-based, pro and con list type of strategies for deciding when to invest in your business (I’ll show you those in a minute… with a quiz!), but I believe that in your gut, you always know when it’s time to take a leap.

 

I asked some awesome entrepreneurs how they know it’s time to invest in a program and here’s what they said:

“When you’re ready to commit to the next chapter of your life, making the investment isn’t so much about paying for the services delivered. Making an investment like this is about making an investment in YOURSELF and saying, ‘Yes to me! Yes to putting my absolute best foot forward. Yes to creating huge, transformational change. Yes to the huge possibilities that are available to me, right here and right now.’”

– Brigit Esselmont, Biddy Tarot

 

“For me I normally know I need to step up, and to stretch myself a bit if I have been stuck on the one thing, or in the one place for a while.

So I know I need an outside perspective, or some new skills or tools to break out of that plateau.

And I normally find that the ‘right’ program/tool/coach is normally a financial stretch too. But I think they need to be, for me at least. Because it also normally means that I am going to be really motivated to make the most of it. I definitely take more significant investments more seriously than ‘inexpensive’ ones, and they always end up paying for themselves.

As for WHAT I choose to invest in, it’s normally whatever is going to help me bust out of that plateau, or solve whatever problem I am stuck on.”

– Kate McKibbin, Secret Bloggers’ Business

Wait! Before you keep reading, I highly recommend taking my free quiz (it’ll be sent to your inbox) so that your answers aren’t affected by my descriptions below:

 

There are 6 questions I ask myself when considering whether or not I should invest in a specific e-course, program, mastermind, coach, conference, etc.:

1. Do I have the money?

This could be in the form of a payment plan, but I need to be able to afford the program. Here’s the catch, as mega blogger Kate McKibbin mentioned in her comment above, I also believe that your investments should push you. They shouldn’t make you starve or afraid that you’ll lose your house, but the best investments push what you think is possible financially.

In short, when you invest heavily in a program, you are way more likely to use it.

2. Does this help me with a need I have right now?

What are you hoping and wishing and praying for help with right now?

You don’t have to know exactly what you need. Oftentimes, it’s hard to know what you need because if you knew you’d already have it! That’s where the gut feeling often comes in.

Do you feel like you need a catalyzing community to pull you out of your income rut and blast through your current glass ceiling?

Do you already have a strategy but need some specific technical training?

Do you need to hire a team member to help you implement?

The more clarity you have here, the likelier it is that you will recognize when the right opportunity pops up!

3. Am I excited about it?

To me, this is the MOST important question. Excitement and enthusiasm cover just about every other problem that you could have. Excitement will help you tighten your budget to pay for the program as well as have the energy to implement the strategies.

I much prefer that you invest in a program that you’re SUPER excited about but aren’t sure why than a program that seems logical but bores you to death.

Your excitement comes from your subconscious computer calculating all of the possibilities and letting you know that YES, THIS IS THE THING YOU NEED. When you get that, “OMG I want to do this!” feeling, beware of doubting it.

4. Will it push me out of my comfort zone?

When I decided to join The Conquer Club in 2013, I was terrified. I couldn’t believe that I was spending $5K on a year-long program and live event. I’d never done anything like that before.

But I was excited beyond belief and knew that the nerves I felt were part of the weirdness we feel when we do something outside of our comfort zones.

There’s a big difference between a bad gut feeling and nerves. A bad gut feeling is an inner knowing that something’s not right. You might get a bad gut feeling when you meet someone who seems sketchy to you. On the other hand, nerves are the butterflies we feel when we’re doing something we don’t know how to do. Every time you step outside of your comfort zone you will feel nervous!

5. Does it come from someone reliable and trustworthy?

I’m a stickler about investing my money in awesome people. I often watch entrepreneurs like a hawk for months before I give them any of my money. It’s not easy for me to part with my hard-earned cash and I want proof that they’re legit before I say yes.

My advice here is to pay attention to referrals and recommendations you get from people you already trust. Always follow someone’s blog and attend their free webinars / watch their free content before you buy something from them. Watch what they DO not what they SAY they will do.

Finally, always invest in programs by people who have achieved a goal that you want to achieve! This should go without saying, but you’d be surprised how many people are coaching “7-figure businesses” to be successful who haven’t even made 6 figures. (Money isn’t everything. This is just an example!)

6. Am I prepared to do the work?

The last thing I ask myself before I click the “enroll now” button is: What do I need to do to make sure that I squeeze EVERY PENNY out of this program?

How much work will I need to do to get my money back from this investment? Is the program going to help me to achieve that kind of result?

Is the price of the program worth the money that I’m investing? Will I have the time to implement the program and get the desired result?

 

Want to know if you’re ready to invest in a specific program? I’ve got a magic ball for that, darlin’!

Let me know in the comments: What’s one program you’re REALLY happy that you invested in and why?