Raking it in without
breaking your soul

Signs You Can Quit Your Day Job

THE LEAP! The leap feels so big. Quitting your day job to launch your own empire is full of so much anxiety, fear, curiosity, hope, and thrill.

Most of us aren’t equipped to sort through that many emotions, all happening at the same time. It’s like the Jungle Juice from your college years. And most of us weren’t equipped to handle that either.

So, while there’s no one path to entrepreneurship, let me help you sort out when you’ll know you’re ready to take that leap.

Money & Insurance

The biggest burning questions I get in my DMs are fears about money and insurance.

If you’re in the position to stay in position, do it. By that I mean, if you’re able to stay in your day job while you grow your empire on the side, that’s the most stable situation. Yes, it’ll mean you’re sacrificing some nights and weekends but if you’re just rewatching Breaking Bad again, you won’t lose much.

When you’re earning 75% of your day job salary through your side empire, you’re in a position to walk.

I mean, I walked without having much lined up. People do it all the time. But ideally you’ve built enough of a bridge to make the leap more like a hop.

You only need to get 75% of your salary covered because once you take the leap you’ll have a lot more time on your hands for business development to get you to 100% +.

The + also includes covering your insurance, which is probably the #1 block for people in the US who have to suffer through employer-based insurance programs. It’ll become a cost of doing business. You can handle it. But now’s the time to research how much you’ll be paying and add this cost to the list of expenses you’ll incur regularly (you’ll use that list to help you figure out your pricing).

Thing is – people get jungle juice feelings about money and insurance but it isn’t the first thing to sort out.

Offer/Service/Product

What the hell do you sell, Honey? You have to start here.

What do you offer in exchange for money? Usually it’s some kind of product or service. To make a successful leap, you’ve gotta articulate exactly what you sell and package it up in a way that potential buyers can clearly understand.

It’s one thing to say “I’m a stylist and I’ll tell you what to wear.” Dime a dozen.

It’s waaaaay more attractive to say “I’ve got a curated box of clothes in your size and style that I’ll mail to you once a season.” THAT I would buy. It’s packaged. Ok, literally – a box of clothes – but conceptually too and that’s the more important part.

And even more important than that is the underlying mechanism you develop to actually deliver the offer. You can’t just *say* you sell a box of clothes, you have to actually set up the processes by which you’ll find out what customers want, establish relationships with stores, think through the packaging (physical this time – the cardboard box you’ll mail).

You need the idea, plus the processes to make the idea happen. Figure that stuff out first.

Client Demand

The second thing you need in order to quit your day job, right after the idea and process, is the clientele. Almost everyone has their first clients long before they get their first logo.

Client demand can start out small – like, you told your idea and process to a friend, who told a friend, who wants to work with you now. Even if you aren’t ready yet, that counts as client demand.

If you find yourself saying no to some potential work because you’re out of hours in the day, that definitely counts as client demand and that’s how you know you can walk… or leap.

(By the way, I used these same signs to help me navigate my process of cutting out some income streams that I don’t like and leaping over to others that bring me more joy – uh, like Boost & Bloom. This ain’t just for the newbie entrepreneur.)

A strong, sustainable empire will also require branding and marketing and systems and strategies and you’ll build all of that as you go. Don’t worry about it now. Just get product, demand, and money sorted out and you’ll be ready to quit your day job.

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Being Strung Along

The thing about being strung along by a “potential client” is that you often don’t know it til it’s too late. Let’s look at what happened to a couple of my students and let their hindsight become your foresight.

No work without a contract.

Sometimes we make it easy to string us along. Like when we agree to work we wouldn’t normally do, for the promise of a future contract.

One of my previous mentees (let’s call her Trudy) accidentally set herself up for being strung along. She realllllllllly wanted to partner with this organization. It woulda been a big fish to add to her portfolio.

In her early conversations with her point of contact at this org, they seemed super eager to work together. So much so, that the client asked Trudy if she’d be willing to jump in on some small tasks (warning sign #1) at a low (warning sign #2) hourly rate (warning sign #3).

Trudy didn’t know me then, so she said yes. The client said it would just be temporary while they write up the bigger contract and get it in place.

Did Trudy ever advance beyond low wage task labor?

No my friend she did not.

And she was too embarrassed about the scope of her work there to ever include this client in her portfolio.

The client doesn’t know what they want.

Another student of mine (code name: Blanche) got stuck in a months-long string-along with a potential client because of “decision by committee.”

Similar to having too many cooks in the kitchen, decision by committee is an excellent way of slowing progress to a casual stroll through I Don’t Know What Do You Think Land. Have you and your partner ever entered into starvation because neither of you could decide what you wanted to eat for dinner? Like that. But with ten partners.

Blanche had a typical initial meeting with this client to lay out the possible solutions she could offer to the problems they were experiencing. They seemed to have come to agreement about the way forward. Blanche went home and waited for a contract.

And waited.

Blanche checked in but by this point, the finer details of the conversation had been lost, so the potential client asked Blanche to write up the plan in a proposal (note to Future Blanche: Write and send the proposal immediately after the initial meeting.)

Blanche sent the proposal and waited.

And waited.

When she checked in again, the potential client said the team needed to really think about whether the proposed solution would solve the right problem. Could Blanche meet with the whole team and help them talk through their problems?

I’m gonna skip to the end of Blanche’s tale: Blanche dealt with so much waffling you’d think she could open an IHOP franchise. This client liked the idea of working with Blanche (or, at least, of having a consultant) but couldn’t ever make a decision about where to start.

I actually suspect they didn’t have the funds to invest in the right solutions but didn’t want to say that to Blanche’s face, so they just let it playyyyyyy out.

Look, some clients really do take months of nurture before the project comes to fruition and you get that sweet contract in your hands. You’ve gotta relationship build. They’ve gotta convince some team members to swipe right on you. Procurement processes and vendor onboarding – the creepy evil twins staring at you blankly at the end of the hallway of consulting life – can take a long, long time.

You’ve gotta learn how to tell the difference between when they really do need time and when they’re stringing you along. Here’s how I tell:

Check-ins should advance the plot.

If you’re not hearing a reply after you send a check-in email, wait a week and send another. We all have those weeks from hell where we can barely breathe. But if you don’t hear anything after the second check-in, move on with your life.

When you do get a reply, it should include some decision or action or next step with a date attached to it.

Like “My team and I have a meeting to discuss this project next Tuesday and I’ll get back to you then.”

or “I have a few more questions. Can we schedule a Zoom to discuss?”

These are check-ins that advance the plot.

If your check-in gets a reply like “Thank you for checking in!” or “We’re still thinking about it.” you’re being strung along and it’s time to walk on by.

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Client Red Flags

“What would the price be if we took out the graph makeovers?”

When I hear this question, I run for the hills. I’ve learned to recognize this request as a giant red flag.

This question reflects a potential client who is gonna be a complete PITA (while most business acronyms are ridiculous, this one is important: Pain In The Ass). And I do not want to work with PITAs.

Just like I didn’t want to date jerks. It can be hard to know who’s a jerk at first, right? Everyone’s got maximum charm and best behavior at the beginning.

But once you get burned, you (and your friends) look back at those seemed-benign-at-the-time comments like “I’m such a feminist – I love women!” with fresh eyes. Hindsight teaches you to recognize red flags.

Same with clients when we get burned.

Collect the lessons and form a red flag checklist.

We each have to DIY our own red flag list. But let me seed yours, ok? The question a potential client posed at the top of this post about what the price would be…. that’s nickel-and-dime behavior.

Here’s what isn’t: “Do you have any government or non-profit discounts?” That question is harmless.

First of all, it’s common. Many places DO offer government and non-profit rates.

Second, I respect the fiduciary obligation to inquire about a deal. I get it – we’ve all got budgets. Doesn’t hurt to ask. Reminds me of the way my grandma looked her budtender right in the eye and asked if he had a senior discount. The chutzpah.

But this question: “What would the price be if we took out the graph makeovers?” is different. It’s saying “Even though you’ve developed a well-thought-out workshop package designed to increase our data visualization capacity as much as possible, can I take it apart bit-by-bit?” Nope.

You don’t have to listen to my experience, if you’re interested in playing with fire.

Let me tell you what happened after I said YES one time. YES, we can take out the graph makeovers and lower the price. You know what came a week later?

“Well, what would the price be if we took out access to the Data Visualization Academy, too?”

Run, my dear.

Because the next step will be a request for an hour-by-hour account of your work.

And not only is that a nickel-and-dime situation that breaks the high-quality package I’ve pulled together, it’s micromanagement. This client is gonna be a PITA.

Yes usually comes from a place of fear. No comes from a place of strength.

It isn’t worth the pain.

My friend Toby made me write down my dating red flag list. He’d pull it out over IPAs in the pub, when the occasion was right. When I was about to make a bad decision and repeat a mistake.

You may need to do the same for your client red flag list. Share it with someone else who can keep you accountable to the higher standards you’re setting for yourself. Write to me with your list and compare yours with that of another entrepreneurial friend.

Your red flag list is how you create boundaries. It’s how you generate an empire where the atmosphere is respect. It saves you from stress headaches and new gray hairs. It’s peace.

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Books Are Not Lucrative

My editor is in my inbox. Again. She gently prods me a couple times a year about writing another book. Or updating an old book. Or writing anything besides newsletters, really.

I’m so resistant.

Writing a book was such a “Should be on my bucket list” notion back when I was in grad school. Before I published a book. Before I knew how much work it would be.

When I was contemplating whether to write it, I was in Indianapolis at a dinner for the keynote speakers of a conference. I was deliberating about this with another keynoter, who told me “Books are your best business card.”

He handed me a copy of his book (yes, he carried copies).

He explained that the book itself won’t make you much money.

Royalties are crap.

Way more recently, I saw this tweet, which validated that things haven’t changed much since then.

By contract, my royalty payments amounted to 14% of sales. Just 14%. For writing the whole damn book (and doing most of the promotion, I might add).

So Mr. Keynoter was saying that the book won’t make you money. But it will open the door for bigger opportunities. You’ll be invited to give keynotes and workshops. You’ll be asked to consult. You can immediately double or triple your prices.

All of those things are 100% true. Publishing a book will not make you rich. You aren’t Stephen King. You don’t get advances. You’ll wait years – literally – after signing the book contract before you’ll see your first royalty check and it’ll be nice but you can’t quit your day job on those dollars.

Writing a book makes you more visible. So if it’s something on your bucket list, the moment you send the manuscript to your editor, you need to start preparing the services (workshops, keynotes, etc) you’ll sell to your new audience.

Books aren’t lucrative.

The opportunities you get from publishing are.

Of course, not everything has to be lucrative. You can write for the pure joy. You can write because you have something to share with the world.

But you don’t need a book to do those things.

See, Mr. Keynoter was advising me at that dinner back before social media became A Thing. Before anyone could start a podcast or a newsletter and grow a following of thousands. Pre-Tik Tok.

15 years ago, books may have been your best business card but now your social media could be even better.

If you want to write, start writing.

Don’t wait for the book deal. Your social media or blog or podcast will likely be the thing that attracts a publisher anyway. So just get to the writing.

Your writing, no matter where you do it, will open up opportunities that make you a lot more money. Writing a book takes months to years of intense focus, patience, and organized thought. Most people underestimate the amount of time and energy required. If you put the same time and energy into your podcast/newsletter/Tik Tok, you’ll get the same opportunities.

If, after reading all of this, you still want to write a book – awesome. Prepare for the opportunities. Get your promotional house in order. Keep writing – that online course, that pitch deck, that story for Forbes.

Once you see that career growth doesn’t come from the book itself, but from the promotion and offers that stem from the book, you might even consider a popular route among many authors I know – self-publishing. Where you keep 100%, not just 14%.

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Two Phrases Every Entrepreneur Should Know

Would you take a wine recommendation from a teenager? Of course not. People want to partner with someone who has experience.

Which is why the question Tom sent me is so common among those of you considering entrepreneurship: “How much experience would you recommend having before going it on your own doing the consulting route? Do I need to consult beforehand?”

Though it might look like it on the surface, this question is not just for newbies.

Seasoned entrepreneurs who want to expand their empires into new (and perhaps more lucrative) markets run into this same issue.

People pivoting to new fields, despite a decade of experience, face the same fear.

No matter how long you’ve been on the block, you need two key phrases in your entrepreneurial vocabulary:

“In my experience with similar situations, I recommend…”

The purpose of this phrase is to convey confidence to your clientele. You can be trusted. You’ve done this sort of thing before.

All this means is that you need enough experience to say I’ve seen this.

You don’t have to have that experience in the same industry you’re trying to break into right now. In fact, your cross-industry experience is an asset.

You don’t have to have that experience through paid work. Real life grad school projects or free time portfolio development exercises absolutely count here.

But the truth is that even though I’ve been in business for a dozen years and I like to think I’ve seen it all, a client will still surprise me every once in a while. That’s why you need this second key phrase:

“I haven’t run across this yet, but I have some ideas and I’ll do some research and get back to you.”

You don’t need to know e-v-e-r-y-t-h-i-n-g but you do need to have the unwavering faith in yourself that you can figure it out.

Talented entrepreneurs can find the answer even if they don’t have it right now. They’re resourceful. They’re also timely – you’ll get those ideas back to your client within 48 hours.

I’ve seen the experience question hold too many would-be successful entrepreneurs back from starting their empires.

How much industry experience did you have before you launched your business? Click here to tell me in an email. My hunch is that it’ll be a very wide range. The path into entrepreneurship has 1,000 different entry points.

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