When You Know You Need a Change But You're Terrified to Make It
I was talking to a good friend yesterday who is in her mid-40s and has been a childcare provider since she was 16. She is at a moment where she wants to shift her life to something new and wider and scarier, and what that exactly looks like, and how it will make her enough money, and if new certifications are required, are all unclear. She has so much amassed experience and interests and could go a few different ways (makeup for film or theater, starter of a children's café space, book writer, and more): how does she decide where to lean and how does she make money while doing it?
After telling me all of these exciting possibilities she really emphasized, "I am so, so scared to do any of it. But I know I have to make a change."
I have heard some version of this from so many people this year, across my career transition clients and friends and family, and even within myself! There's something about this particular moment: maybe it's post-pandemic recalibration, maybe it's an economy that feels like it's shifting under our feet, maybe it's watching entire job categories shrink or disappear (a lot of my clients are former TV comedy writers, for example, which is a type of job that just doesn't exist the way it used to). But the theme keeps surfacing: I want something different. I don't know exactly what. And I'm terrified.
I will be honest that the fear is not going to disappear. It just isn't. But here are some things you can do to push forward anyway:
1. Look for confidence from those around you
This friend isn't sure of herself when it comes to these potential directions, but I have known her long enough (and even seen her work) and I know how dedicated, smart, and impactful she is. I will continue telling her that over and over.
Here's the thing: when you're in the middle of your own fog, you can't see yourself clearly. But the people who love you and have watched you operate? They've been taking notes this whole time. They remember that event you pulled off effortlessly. They remember how the kids you cared for still send you cards a decade later. They remember you troubleshooting something impossible and making it work anyway.
If she trusts me (and allows my confidence to overshadow her doubt, even just a little bit) she'll make strides. You might need to borrow someone else's belief in you for a while. That's allowed. That's actually what community is for.
2. Determine what ENOUGH money is while you make this transition
This is a practical step that a lot of people skip because it feels unromantic or limiting, but it's actually liberating. What is the actual number you need each month to cover your essentials and not spiral into financial anxiety? Not thriving money. Not savings-padding money. Just: what keeps the lights on and the panic at bay?
Write it down. Be specific. Because once you know that number, you can reverse-engineer a plan. And you often realize it's lower than you feared, which opens up more room for experimentation than you thought you had.
3. Do the old work (or another temporary position) enough to get enough money to not feel stressed all the time
This one is about buying yourself breathing room. You don't have to quit cold turkey. You don't have to burn the boats. You can keep one foot in the old world while you test the waters of the new one, and honestly, that's often the healthiest way to do it.
Seasonal work. Part-time contracts. A few clients from your previous life. Whatever gives you that baseline income from step two so that your nervous system isn't in constant overdrive. You cannot think creatively about your future when you're worried about rent. Give yourself the stability to dream.
4. Make a list of experiments
What are the things you could do NEXT towards any or all of the directions you're considering? Not "build the whole business": just the next small thing.
For my friend, this might look like: shadow someone doing makeup for a local theater production. Have coffee with a café owner and ask what surprised them most about opening. Write one essay and see how it feels.
Rank these experiments in terms of your ability to do them soon and with a low barrier to entry. The goal here is momentum, not perfection. You're not committing to a path: you're just gathering data about what lights you up and what doesn't.
5. Make a list of people you could talk to who know more about the directions you're curious about
This is where things start to get real. Most of us know people (or know people who know people) who are doing some version of what we're dreaming about. But reaching out feels vulnerable. It requires admitting you don't have it all figured out. It asks you to say, "I'm interested in this thing and I don't know where to start."
So: make a list of those people. Then rank them in terms of comfort reaching out and being vulnerable with them. Start with the person you are most comfortable with, have that conversation, and then work your way down. Each conversation gets a little easier than the last.
6. Identify the super-connectors
Within that list, look for the super-connectors: the people who seem to know everyone, who light up at the chance to make introductions, who can open doors you didn't even know existed.
I'm planning to connect my friend with someone who is in wardrobe at Wicked on Broadway and someone who used to do makeup and hair for film. She didn't ask me for this. But I know these people, and I know her, and my job as someone who believes in her is to create the conditions for the experiment. Maybe one of those conversations leads nowhere. Maybe one of them cracks everything open. You don't know until you try.
The fear doesn't go away. You don't wake up one morning suddenly brave. But you can build a scaffolding of practical steps and borrowed confidence and small experiments, and that scaffolding holds you up while you figure it out.
My friend is scared. She's also closer than she thinks. And if you recognize yourself in her story, you probably are too.
So: what's one small experiment you could try this week?
