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How Will I Make Money Doing That?

This is the most frequent fear I hear from clients who are contemplating a career change. Worrying about how you will make money while dreaming about your ideal career is like being doused with cold water while sleeping—disruptive at best, completely unnerving at worst. Here are some tips for how to allow yourself to dream about your ideal career AND figure out how you’re going to make money.

Create a Dreaming Sandbox
(The kind kids play in, not the one the cat uses.)
In the Internet world, web developers have what they call a “sandbox.” This is a web-based environment solely for the developer where she can play with new code and see how it works on a pseudo-version of the website, without messing up anything on the real site.

Create your own Dreaming Sandbox where you allow yourself to play with new ideas. Don’t worry if the ideas you’re playing with can make it in the real world or not, just allow them to form and evolve. Have fun with it, let yourself have silly, impractical ideas. Letting yourself have those ideas will lead you down paths you’ve never before explored.

Put Your Fears in the Parking Lot
As you allow yourself to start dreaming, fears will inevitably come up. Write down your fears and put them aside—I call it the “Parking Lot”—to deal with later. This way you aren’t resisting the fears, but you also aren’t letting them get in the way of the creative process.

Solve for Career and Money as Two Separate Problems
Note how you feel when you say the below statements to yourself:

Statement 1
I really want to be a <insert career idea here> but I also need to make <insert amount of money>.

vs.
Statement 2
I really want to be a <insert career idea>; what’s the next step to move toward it?
AND
I would like to make <insert amount of money>, how can I do that?

I’m guessing Statement 2 feels better. Perhaps it even blew your mind a bit with new possibilities you hadn’t considered before. When you join the questions “What will I do?” and “How will I make money?” you are requiring your dream to deliver the financial goods right away. This often feels like an insurmountable problem, so we stop dreaming. When you separate these questions, new possibilities unfold. Suddenly there are many ways to move toward your heart’s desire and make money along the way.

The next time someone asks you how you’ll make money pursuing your dream, tell them you’ll do it the same way you always have—with style, creativity, and a little elbow grease.

P.S.

If you live in Seattle, check out my upcoming Mastering Money workshop.

Overworked? Share the Pain

I was at an event the other night and struck up a conversation with “Michelle” who was looking stressed and a little exhausted. She told me she’s been regularly working 65+ hours per week—she was not happy about it.

When I asked her why she was working so many hours, she said they just keep giving her more work. I could tell right away that Michelle was the glue person at work. The one who stays late, gets things done, doesn’t complain too loudly and generally holds everything together. The problem with the glue person is that they tend to fall apart (pun intended).  

I have this theory. Humans won’t substantially change their behavior unless they feel some degree of pain. I explained to her that while she’s in “pain” in terms of how many hours she’s working, no one else at her work is feeling that pain. Even though she is telling her superiors she’s too busy, they are not directly feeling the pain of her workload. Hence, they aren’t highly motivated to act. This doesn’t make Michelle’s superiors evil, they simply aren’t uncomfortable enough to make alleviating Michelle’s workload a priority. Simple human nature.

Instead of continuing to absorb an unsustainable workload (or burn out, or quit) Michelle’s new mission is to share the pain. Once her bosses feel some of the pain—which could come in the form of missed deadlines, customer complaints, or simply having to spend more time helping her prioritize—they will become more motivated to make a change. Her pain will now be their pain. My favorite tool for doing this is called—well, I don’t have a fancy name for it, but here’s how it works. The next time Michelle’s bosses assign her a new project, she says:

“Sure, I’m happy to work on that. I have these 6 other projects I’m working on, so if I take this one, two others will need to move out of my queue. Which ones would you like to move?”

This strategy is brilliant on so many levels:

• Michelle still appears to be a team player by demonstrating willingness to take on new projects.
• She now can decide how many projects she can do within reasonable working hours.
• Her bosses get to choose what they want her to be working on making it hard for them to argue with the line she’s drawn.
• Michelle’s bosses now clearly understand what will not get done (feeling her pain!) and are placed in the position to have to deal it.
• By the same token, if something slips through the cracks, Michelle is not to blame because everyone has agreed upon the priorities.
• Michelle is no longer resentful because she’s now actively managing her workload (and her superiors).

The key to making this work is to stop working so much. If you try this, you might have thoughts come up like I should be handling all this or I’m letting people down. Question the truth of these thoughts—who are you really letting down if you keep working like this? How much longer will you last? How is the quality of your work? How’s the rest of your life going? Exactly. Work through those thoughts and hold the line. Then enjoy your newfound free time and plucky attitude.

Bosses Gone Wild

Back in the day when I was but a young online marketing ingénue, I was living the idyllic life, working for a mentor I adored as part of a smart, cohesive and fun team (at least that’s how I remember it). Then, my first corporate reorg occurred and I found out effective immediately, I would be moving to Team X and reporting to my new boss, I’ll call him “Tad.” Tad was the new exec on the block and had a reputation for “shaking things up” and “straight talk.” Little did I know at the time that this is code-speak for this guy is a megalomaniacal jerk.  

Team X and Tad had a different vibe. Tad lead his team with a unique mix of bombast, intimidation, and manipulation with just a dash of sexual harassment to keep things interesting. Tad’s favorite thing to do was call the team together and yell at/lecture us on obscure sociological topics for up to 3 hours at a time (I’m not exaggerating). Fun. Needless to say I did not respond well to this management style.

One day, Tad tracked me down and called me to his office. I managed to avoid him most of the time since I worked in another building. Then, with his office door open, he tore into me about some perceived mistake I made. To top it off, he then proceeded to deliver a pandering lecture that was supposed to “help” me “get” whatever he perceived I wasn’t getting. All of this within clear earshot of all my coworkers and lasting for a couple of hours. To this day I still cringe at the thought of dodging the spittle while sitting there enduring his tirade and trying not to cry (I didn’t thank god). I was humiliated, angry and ready to walk right out the door.

Why?

That’s not a question I could ask much less answer at that time. I spent a lot of time feeling victimized by Tad and eventually threatened to quit my job if I wasn’t moved to another manager (not a recommended move unless you’re really ready to walk). There was practically a take-a-ticket machine at HR for Tad by this time so it came as no surprise to the powers-that-be. But why did Tad’s tirades make me feel so bad?

Because I believed him.

I was insecure and intimidated by him and others around me. I believed I was not as smart as the rest of Team X so Tad’s tirades felt like a knife in my heart. This is an important distinction—it wasn’t Tad’s words that were cutting me, it was my THOUGHTS about his words.

What if I hadn’t believed Tad? What if I completely believed that I was smart, talented and that nothing bad would happen to me no matter what he said? I’ll tell you what would’ve happened—it would’ve been a much shorter meeting. If I didn’t believe what Tad is saying, I wouldn’t have attached to it emotionally, which would have allowed me to use my rational mind to extract myself from the situation—and would’ve made me a much less attractive target for his tirade. (People like this pick up insecurity like a scent and will go for the jugular every time.)

Here’s how it could’ve gone had I not believed what he was saying:

Tad: Bridgette, you totally screwed up the TPS report.

Bridgette: Hmmm, can you give me more specifics about what you expected to see?

Tad: Well, you should’ve attached the cover sheet to the TPS report thusly.

Bridgette: Ok Tad, I’ll make sure to do that next time. Later.

I can tell you that I wouldn’t have hung around for hours of verbal abuse. When I believe I’m worthy, there are a million ways to handle this situation, most of them involving a very short conversation. When I’m emotionally attached, I shut down and become stuck.

I couldn’t change Tad (turns out Tad couldn’t change himself and was eventually fired), but I could’ve changed my thoughts about the situation. When you don’t believe something is true, it’s impossible for someone else to attack or victimize you. What they are saying will literally seem bizarre or even laughable to you—it’s just not real. Try it and see what happens.