Should you take the money?

“Hi Ninjas,

I’m just a few days in and the Emergency Turnaround Clinic is already working. It’s only Thursday morning of the first week, and I am already feeling a shift. I took a leap of faith and decided to follow in your footsteps with pay what you can.

So, Monday, I slapped up a post offering my creativity consulting services for whatever people can afford through the end of April. I also decided to offer a giveaway for three free sessions, winners drawn at random, for anyone who shared the post on social media and left a comment.

And… crickets. So I asked several of my well connected, hustling friends to share it yesterday (why was this hard for me? I share their stuff all the time) and woke up this morning to find that I had a couple of comments from people hoping to win a freebie and two new pay what you can consults lined up.

It’s not a ton of money, but it is forward motion. Things are starting, finally. It was the little push of encouragement I needed to keep going.

The one issue I’m facing is that I am buried in freelance writing work, and squeezing in little bits of time here and there for the ittybiz that is my one true love is hard. I can’t afford to lose that writing income just yet. My over the top supportive partner suggested using her tax return to buy me a new laptop (mine is dying a hideously slow death) and to cover the income I would normally make in two weeks of freelance writing.

This is all so that I can have those two weeks to fully focus on my business and crank out some products. This is so generous and wonderful, yet feels so risky. What do you think? Should I take her up on the offer and just do it with the trust that the time I put into it won’t be wasted?

Thanks for all you do.”

Naomi’s Answer!

First, congratulations. You have said something very important here when you said this:

“Things are starting, finally.”

Yes. That.

When you are in the beginning stages, “starting, finally” is what it’s all about. It doesn’t look anything like the dream yet. It doesn’t look like what those people in those videos said it would look like. In fact, they never said anything about this part.

Like, they said it would take hard work, but they never talked about the despair. Interestingly, the despair never came up. The mental machinations and ghostly whispers and messing with your head that happens when the crickets chirp. Maybe they mentioned the crickets chirping once, in passing, but it seemed to flutter by in a flurry of cheerful “I LOVE MY LIFE AND MY BUSINESS YES ALL OF IT EVERY SINGLE BIT YUP MMMHMM EVERYTHING IS GREAT NOTHING TO SEE HERE PLEASE DISPERSE.”

And who can blame them? Who wants to go back there? What Fancy Big Shot Business Guru (TM) wants to go back to the awful places? (Please see exhibits: Awful Place A, Awful Place B, Awful Place C, and the Awful Place Retrospective.) What Fancy Big Shot Business Guru (TM) wants to admit that they’re still there? That actually, they just moved back in with their mother? That they really thought they’d be buying better dog food by now?

So you’re in uncharted waters here. I mean, they’re not really uncharted. Everybody who’s ever done anything with their life has those waters quite well charted indeed, thank you, but nobody’s going to show you their charts because, well, see above. For your purposes, the crickets and the leaps of faith and everything that happens before the “starting, finally” may as well be uncharted. So on behalf of both of us, you have our admiration, our empathy, and our respect.


You asked a question and I will step off my soapbox long enough to answer it.

Your over the top supportive partner has offered you the chance at a First World laptop and some space to breathe and progress and do what matters.

Dave and I are going to do a She Said, He Said and he is going to answer your question practically tomorrow. In the meantime, I will give you my abstract, conceptual, hippie moon altar answer and together, they might actually help. (Results not typical. Help sold separately. See store for details.)

Let us look at your question in detail.

“This is so generous and wonderful, yet feels so RISKY. What do you think? Should I take her up on the offer and just do it with the TRUST that the time I put into it won’t be WASTED?”

The answer to your question lies in the three highlighted words.




First, we must look at what you feel is at risk.

It could be money. (Doubtless Dave will address this tomorrow.) It could be credibility. It could be concerns of the teensiest weensiest agenda buried in her offer. It could be fear of success. It could be fear of failure.

Once upon a time, when Jamie worked for a Very Big Bank, he was hating his life. (This was naturally before he met me.) He did not like working at the Very Big Bank. He wanted to do something else. I’m pretty sure he wanted to do anything else. He was depressed and it sucked.

When asked why he did not leave the bank, he gave a very logical reason:

“Because if I quit the bank and I’m still unhappy, I won’t have quitting the bank to look forward to.”

When you are not depressed and hating every part of your work, this answer sounds illogical.

When you are depressed and hating every part of your work, this answer sounds like the most reasonable thing in the world.

It is possible that some of the risk you feel is the fear that if you do it, you will lose your dream by making it a reality. (See: 7 Reasons I Decided Not To Become A Prostitute.)

There are many things that could be raising the risk flag. Only you know which of those reasons apply to you. You may want to journal on this or something.

Now let’s look at trust.

This is an interesting word choice. What must we trust? In whom are we placing our trust?

Are we trusting your partner to be gracious and not hold it over your head for the rest of your life?

Are we trusting God that nothing unexpected comes up?

Are we trusting you to make good use of the time and not spend it all watching Irish priests sing Leonard Cohen songs at weddings?

Are we trusting that the work that will be done will achieve the ultimate desired outcome? (Like, she gives you time and money to write a book and you’re not worried the book won’t get written… you’re worried the book won’t get bought.)

So the next question you must ask yourself is what or who are you trusting? You may want to journal on this or something.

Last, let’s take a look at wasted.

We must consider what would make this time and money a waste. To do that, we must consider what would make it a success. (What constitutes success?)

Those who strongly believe that the thing they need most in the world is a new laptop and two weeks to work generally do not tend to worry that the time will be wasted. (They are usually overconfident to the point of hubris and utterly delusional, but still.) These are the people who do not witness at home but want their parents to spring for a mission trip, or those who do not write at home but want their husband to pony up a writing retreat.

If it is even occurring to you that this time might be wasted, you are showing tremendous maturity and self-awareness. This is a real concern, and you must observe and analyze it.

Why might it be wasted?

It is possible that, again, you are concerned that the outcome of the time will not be lucrative. Like, you’ll get your website up but nobody will buy. It is possible that for you, that is wasteful.

It is possible that you are so burnt out by freelancing that your body knows that two weeks to work on The Real Thing will actually get spent sleeping, crying, and watching reality television.

It is possible that you’ve felt this way before, needing time and resources, and you haven’t used it for its intended purpose, and you felt like a fraud and a fake.

So what would make it a waste? What would make it not a waste? You may want to journal on this or something.

My actual answer.

This is a decision point for you, a point when, if you choose one direction, your narrative will be permanently altered and you don’t yet know how. These are hard calls to make. They force us to assess existential stuff that we can usually avoid in the busyness of life, love, and a freelancing business.

I will tell you what I would do, although it probably won’t help the weight you’re feeling.

I would first ask myself, “Is my partner the kind of person who makes covert contracts and holds things over my head for the rest of my life?”

I would then ask myself, “Will losing this money put her in a position of pain, loss or financial jeopardy?”

  • If the answer to both questions is no, I would take the money. Doing brave new things to brighten our futures is what separates us from the meerkats. Go for it. It will be hard. There will probably be some negative consequences. It’s probably worth doing anyway.
  • If the answer to the first question is no and the answer to the second question is yes, I would take the money for the laptop but not the time off. The new laptop would inspire me to freelance my little booty off to save the Take Time Off money fast.
  • If the answer to the first question is yes and the answer to the second question is no, I would take the money, build my dream, and if she doesn’t learn to behave like a decent human being in the interim, then dump her. We don’t spend our lives with yucky people. It is not the IttyBiz way.

If the answer to both questions is yes, I would move back in with my mother.

Please tune in tomorrow for Dave’s response. It is probably far more practical than my own.

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