Do You Want to Radically Change Your Life, and You’re a Bit Scared to Do It?

I think it is not controversial to say that the lives of 20-, 30-, and 40-somethings change all the time. A new job. Moving. Getting married. Having kids. Another new job. Moving in together. Breaking up. Going back to school. Getting married. Another new job.

And sometimes you might want to Change Everything At The Same Time.

In the last few months, for example, two of my clients have decided to quit their jobs, take an extended (many months) break from work, and move to a new state. One had another job lined up at the other end. One doesn’t, in large part because she doesn’t know what she wants to do next, other than “not what I’m doing now.”

In these cases, life in 3 weeks, let alone 3 months or 3 years, is utterly (deliciously? frightfully?) up in the air. To my clients’ credit, they just freaking went ahead and did it. But they were really hoping I could make them feel good about the decision they’d made. (And I totally could.)

Are you contemplating such a big change? And are you, not to mince words, scared to do it?

Guarantees, Not So Much. Reassurances, Sure.

Do you want someone to tell you it’ll be fine to upend your life? That you’ll be totally settled in your new life in 8 months and you’ll have figured out what you want in life by then? That you will not end up a bag lady feeding cats under an overpass?

No one can give you guarantees about how things will turn out. In any situation. In this way, changing everything at once perhaps shouldn’t feel as scary as it does: because even if you were planning to keep everything the same…whoops! Life happens.

But what you can do (and what I do with my clients) is to play around with what your life could look like over the next few years. Let’s pick a variety of reasonable paths forward and see how they unfold.

• Do you stay out of work for 8 months and then find an entry-level job in your new career paying half what you earn now?
• Do you return to the same kind of job?
• Do you end up deciding to go back to school after 6 months to get trained in something else?
• Do you buy a home in your new town in a year because you love it so much you’re never leaving?
• Do you increase your spending a lot because, by gum, I’m going to enjoy this time in New York City/Paris/Dubuque?

It’s easy for me, with my fancy financial planning software, to model all sorts of these scenarios. A little harder for you, of course, but honestly you can probably still do justice to it on a yellow pad with pen. Or Google sheets.

Either way, you should look at a pretty wide breadth of possibilities. Do all these possible paths feel okay to you? Do any of them intimidate you?

Now, I wouldn’t be able to give everyone reassurance it’ll probably work out okay.

Being able to make huge changes like this is really quite a privilege,

based on having a nice war chest of money to begin with, or a partner who makes a good income, or family who can support you in an emergency, or highly employable skills, or no one who’s relying on you financially.

Prepare for Opportunities.

Again, you simply cannot know how your life will unfold. Even if you have a job and a home and a family today. But especially if you have no job and you’re moving and you’re about to get married or have a baby.

That doesn’t mean you close your eyes and jump.

There are things that are certain, aside from death and taxes. Namely, sh*t happens, and awesome stuff happens. You just don’t know when or what. Make sure you’re prepared for both.

My business coach puts this in a more lady-like way (which is surprising, knowing her): preparing for opportunities, and building resilience.

What might happen to you over the next little while that could be really awesome? What could those opportunities be?

• Could you get an offer for a dream job?
• Learn about a travel opportunity that you’ve been dreaming about for years?
• See an opportunity to start your own business?

Sure, if you’re not prepared for these, you could always do something sub-optimal like withdrawing money from your IRAs prematurely. Or asking the Bank of Mom & Dad for a loan. Or putting it on credit.

Instead, what can you do now so that if these opportunities arise, you can take advantage easily, quickly, and without too much fear?

• Do you set aside a wacking chunk of cash, more than you need for what you’re planning to do? Cash is delightful in this way.
• Think about what you’d want to do if those opportunities came up. Would it be worth cutting short your sabbatical to take a dream job? Or changing your plans to sit around contemplating your navel in order to do that awesome travel?
• Are there sources of money or support you can rely on if an opportunity comes up that you think is awesome but you don’t quite have the cash to do it? Could you sell more company stock, even if it’s just dropped in value? Do you have a Roth IRA you could withdraw contribution money from (which you can do without penalty or tax)?  Are your parents or spouse willing to cough it up?

Build Resilience.

Now let’s talk downside. No conversation about completely upending your life is complete without considering what could go wrong. And how you might respond.

• Could you have trouble finding a job and it takes 2 years instead of 2 months? (At some point the tech industry is going to crash again, and when it happens, this is absolutely a reasonable scenario to contemplate.)
• Could family concerns arise that require your time or money?
• Could your investments, particularly that bucket of company stock you’re clinging to, lose half their value?
• Could the birth of your child not go as planned and you end up needing to recover for a year instead of a few months?

Obviously, sh*t happens in a variety of ways, and we can’t predict them all. But what are the most likely things to go south in your world?

What could you do if any of those things happened? How can you minimize the effects if they do happen?

• Do you have other kinds of jobs you know how to do?
• Could you reduce your spending a lot to make your savings stretch? How would you do that?
• Do you have the proper insurance to protect you against catastrophic losses?
• Do you have a big enough cash cushion to get you through an emergency? Could you work a little longer at your current job to build up a bigger cushion?
• Could you make some professional connections that might help you at the other end of your journey?
• Do you have family or friends you could turn to for help, if push comes to shove?
• Do you have the right kinds of insurance, to protect at least against catastrophic loss? Renters, health, life, auto.

A Case Study

Let me tell you about one of my clients. She’s in her young 30s. She has a net worth of over $1M (through both diligence and luck).  She wants to change her whole life around: quit her job (at a prominent tech company, where she was paid very nicely), get engaged, move far away, without knowing what she wants to do, but brimming with ideas about a fulfilling, post-tech life. And she’s nervous about it.

I cannot reasonably prescribe her a single path forward. Because, in reality, she has (and I think I mean this literally) an infinitude of paths forward that would be reasonable. She could spend every last penny tomorrow (save that all-important emergency fund) and start rebuilding her finances the next day and have a realistic chance of building a good life for herself. After all, there are plenty of people who have no savings by their mid-30s, and if they start saving then, they should be fine.

So, we walked through a bunch of different scenarios that were both conservative and optimistic:

• Changing to a new career that paid way less
• Starting her own freelance business that took a few years to build income
• Moving out of country for a few years
• Having kids
• Buying a home

She understands that these are all hypothetical, but she walked away from that conversation greatly reassured that She’d Be Okay. She’s got (a lot of) wiggle room. She’s got (a lot of) resources to figure out how to make the next stage of her life exactly what she wants.

Urf.

This is not my best blog post. I feel as if these ideas are still too unshaped, so I’m sorry for that. But I get so excited by the possibilities that exist for women in tech that I wanted to start a discussion about how to approach the wide-open world of possibilities. I hope, despite the need for a few dozen more revisions, that this post has started you thinking about how you can make good changes in your life, even if the notion is scary.

Are you itching to change it all up but want some reassurance that you won’t be shooting yourself in the foot? Reach out to me at  or schedule a free consultation.

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