I don't know about you, but I have always thought of myself as an entrepreneurial person. I'm scrappy. I'm creative. I can make things happen that seemed impossible - then, poof! They're a thing.

It felt mildly inevitable that one day I'd go into business for myself - especially because I kept making all my bosses furious by noticing what didn't work and identifying (unsolicited) solutions to make those things work better. When you're like this, at first, people applaud your initiative. After a while, though, whew! They start to get the shakes when they see an email from you (an actual event that for real happened to my last boss very shortly before I said, "I'm gonna go over here and be a consultant now, byeeee!").

The thing I realized at that "farewell" moment, is that I have always been a consultant - and that instead of driving everybody mad (in all the ways) with my ideas, I could get paid for those very same ideas - which, if you skim the surface of it, seems like a no brainer.

So, when people come to me and ask, "Hey! I'm very tired of having this job, should I be a consultant? It seems like you're having fun." I start with some questions - and they might not be the ones you'd imagine.

Let me add: most of these questions are framed for people thinking about being a consultant for nonprofit organizations - that's where I started, and where I've spent the most time to date. I've noticed a lot of people who dip their toes into consulting jump right back out - after losing some valuable time, money, and self-confidence - and I have some ideas about common challenges those of us who came up through the nonprofit sector face.

1. How Comfortable Am I With Self-Promotion?

When we work in nonprofits - and other organizations, to a degree - we get really great at promoting and celebrating the mission, the product, the anything-but-ourselves-ness of the greater entity. We rarely have occasion, need, or, frankly, an appropriate platform to promote ourselves. This is fine when we're one of many, all working toward a common goal together. But when it comes down to "I have to be seen so I can sell something or I won't eat this month," self-promotion becomes an all-out must-do.

If you aren't comfortable with Self-Promotion just yet, sit with that feeling of discomfort, and get curious. Where does that come from? What are your beliefs about people who draw attention to themselves? Might you be able to move through some of those beliefs and replace the ones that aren't working for you with ones that support a positive view of self-promotion?

Bonus soul work: Who is your Golden Shadow? Your Golden Shadow is someone you admire, someone who is seen by many, but who is so awesome you can hardly imagine you have even a tiny thing in common with them. They are so shiny and amazing, you just look at them from afar and think, "holy wow, if only I could be that fantastic." A lot of people I know mention Oprah, or Tony Robbins, or, in my case, Brene Brown. As you think about your Golden Shadow, consider the ways you might just be a little bit like them. Indulge in that strange experience for a while. And imagine if Oprah, or Tony Robbins, or Brene Brown were too freaked out about self-promotion to get their work out there? What good would that do for the world?

Ask yourself the same thing about your own freaked-outedness about self-promotion.

Can you get to a place where this feels natural and good?

2. How Do I Feel about Money?

This is another common thread I see in my clients - whether they are nonprofit consultants, healers, or artists - they all have something of great altruistic value to offer the world - and they are also very uncomfortable, in general, about the concept of money.

We all have embedded cultural beliefs about money. A lot of those beliefs lead us to feel shame, fear, or other emotions we perceive as negative or painful.

The problem is, those beliefs and the resulting emotions are not helpful to us when it comes to the true fact that we need money to put food on the table, a roof over our heads, shoes on our feet, and gas in the car (or pedals on the bike? I don't know how you use transportation).

When it comes to our money hangups, I have to say, it's one of the greatest obstacles to our ability to successfully ask for, obtain, and keep money flowing through our lives.

A lot of coaches talk about "mindset" as if all you need to do to be comfortable with, rolling in, and shooting money out of your butt all day is to "believe in abundance" and "act as if." I am a HUGE believer in magical thinking - but never, ever when it causes more harm than good. This particular "mindset" teaching that is so ubiquitous is problematic because it blames people for a financial situation that is more systemic and cultural than it is any one person's individual failure. It also easily gets twisted to get you to just buy one more $997 online course because if you invest in yourself even if you're going bankrupt, you'll finally pull this through and make it happen, and the only thing in the way of your success is your mindset! BULLHONKY. There are a lot of things in the way of success - and some of it comes from our self-defeating beliefs (again, culturally implanted - it's not like you woke up one morning and had the completely original thought that "money doesn't grow on trees," and started walking around in fearful scarcity all the time)...

WHEW! This became quite the rant. OK. So, back to the point.

That said, you do need to look at and understand how you feel and what you believe about money, because in order to be successful in business, you do need to get someone to pay you money in exchange for goods or services. It's pretty simple, really. You have to be comfortable with the concept overall, the idea that you and what you offer are worthy of being paid, and you have to learn - over time (it gets easier and easier, I promise!) to talk about money with your prospective clients. And then, you have to bill them, and collect the money. And then! Then, you have to make decisions about that money, where to put it, where to invest it, how and when and how much to pay yourself, and so-forth. You and money, in other words, need to become super-tight buds.

So. What are your beliefs about money? Which ones are helpful? Which ones would you like to swap out for more helpful beliefs? How can you get as magical as you need to about money (law of attraction, anybody?) without getting stuck in self-blaming or using "mindset" as an excuse for inaction?

3. How Do I Feel About Selling All the Time?

This is related to the first question around Self-Promotion. Where Self-Promotion is more about making people aware of you, selling is about inviting them into your world so you can deliver the amazing value you have to offer them. Selling, for a lot of people - not even just nonprofit people, but a LOT of people - feels really icky. It conjures images of the once-ubiquitous telemarketer calls just at the moment you're sitting down to eat dinner with your angelic family. It makes people think of pushy, used-car salesmen (no offense if you're a used car salesman - I get it - I used to be a telemarketer, and guess when my shift was?), and people trying to pressure or manipulate you into buying stuff.

Here's the thing. We think all of that for a reason, because for a really long time, sales has often been a coercive, icky thing. It doesn't have to be that even a little bit, though. We can do sales without selling out. We can make offers without it feeling like you're trying to trick someone into giving you their money.

So, where are you with the idea of selling right now? Do you feel good about it? Take a pen and paper, and write down all the words you associate with selling. Look at them - are they positive, negative? A mix of both? Which is more prevalent in your list - the positive or negative connotations with sales? If it's mostly negative, what could you do to shift your thinking on that front?

4. How Well Do I Handle Uncertainty?

No matter how amazing you are, how healthy and magical your "money mindset" are, how much your potential clients and audiences absolutely adore you, you will go through some times when you have a ridiculous amount of business, complete with a lot of money coming in all at once, and then......crickets (complete with tumbleweed blowing through your bank accounts, and awkward calls from your banker - not that I have ever experienced that, ahem, moving on).

Being in business for yourself is a gamble. It is replete with pitfalls. It is a constant challenge to evolve into a more brilliant and wonderful version of yourself (and sometimes that evolution is aided by dark and difficult times...sadly, we often learn fastest in those times). Uncertainty is a given. Our ability to feel confident, comfortable, and at ease (or, I mean, not screaming, naked in the streets most days) in the middle of uncertainty is critical to our ability to be successful in business long-term. Are jobs a guarantee of security or financial stability? Absolutely not. Do they feel a helluva lot closer to a guarantee of such than being an entrepreneur? Um. Yeah. Duh.

When you're in business for yourself, you are...just yourself. At least at first. And when other people join your business, you get to also be responsible for their livelihoods too! Hooray! More responsibility! Do these things get you excited? Do you have a certain cock to your jaw when you think of it, gritting your teeth with determination? Do you gaze at the financial roller coaster of entrepreneurship with a steely, yet loving eye?

Or, does this make you feel queazy and like you'd rather muck out a stable or change a dirty diaper, or anything, really, that isn't starting a business?

A little of both?

The question of uncertainty is important. It's important to know your temperament. It's not that being really uncomfortable with uncertainty is bad - it just means you need to take different steps to make sure you can get through it with grace and poise when your well is running dry for a time. And if uncertainty is your jam and you live for the suspense of the edge? Great. That will make this more fun.

5. Do I Still Really Want to Do This, Even With All These Considerations?

After allllllll these questions have filtered through your heart, head, and guts, do you still feel like consulting is the thing for you? Do you still feel so full of amazing ideas, innovations, expertise, and that certain something that you're ready to file an LLC right this minute and go for it? Sweeeet!

If you don't, that's OK. Consulting might still be for you - it's just something to enter into thoughtfully, and with a plan. I thought about consulting very seriously for fully 18 months before I finally took the plunge and went for it. And when I went for it, I walked out of my former organization with a contract to provide them with services for a year. That made my first steps into the business really easy - which is great, because there have been a lot of really challenging times (and even more amazing times) between then and now.

I want to add one more thing to think about. If you need to leave your job because you're burned out, it's especially important to be thoughtful and careful about how you move into business on your own. I was burnt to a crisp when I left my organization - I took a nap for four months in between writing grants and doing little things for my former employers. I was still burned out until maybe last summer - which was three years after I quit that job. If you are thinking about starting your own thing, but you think you might be burned out, talk to me. For real. I have a way to go from Burned Out to In Business without building up a bunch of nonsense that will just get you all burned out again (or thwart your success in the first place).

Consulting is Fun and Also the Worst, Sometimes

Just like everything else! It's the best and the worst - the most fun and the least. It's all the things. I wouldn't have it any other way - and if, after reading this gamut of "are you sure??? are you really, really sure???" you are still, in fact, really, really sure, brilliant! Hit me up with a comment here, because I want to know what you're doing!

Sarai Johnson is the best-selling author of a few books, the founder of Lean Nonprofit, and Sarai-Johnson.com, and a transformative speaker, and coach. She helps audacious souls bring their sacred work to life in the world without burning out or selling out, and currently works with nonprofit consultants, healers, and artists to help them make more money so they can go about the business of changing the world for the better. Sarai is a Book Yourself Solid® Certified Coach, GrowthWheel® Certified Business Advisor, Certified Cognitive Behavioral Group Facilitator and 200-RYT Yoga Instructor.

Check out the upcoming Book Yourself Solid® for Nonprofit Consultants coaching cohort program launching in August 2018 here (FYI, it is more than $997 by a little, but the point is, you should be totally cool with investing that money in yourself and your business if the time is right for you - and don't do it because you think Sarai can magically make you rich without you putting in the work, because it totally doesn't work like that). Learn more about Sarai's work here, here, and here.