Talisman Talk


May 08, 2023

Jumping Out of a Career Airplane: How Self-Reliant Women Can Land Safely

By Jennifer Kirby, CIMA®, CSRIC® |

When I speak with women who are self-reliant and depend on their own financial capabilities, they often tell me they reach a point in their careers where they feel malaise, a lack of interest in clinging to jobs, grabbing titles, or elbowing their way up the ladder in corporate structures that weren’t made for them. But they often have a hard time figuring out how to transition to an alternative—a new career, a business, or a way to monetize their skills differently. They want to feel empowered, but rightly fear the loss of financial security. These women want independence, but a move can feel dangerous. But with the right risk management, it’s very do-able.

I refer to such transitions as jumping out of a career airplane. And what does one need when they jump out of an airplane? A parachute.

Personally, I've successfully jumped out of three career airplanes. I started out in film and television production, transitioned to nonprofit fundraising and leadership, and now run my own wealth management and financial advice practice. It was worth it despite all the uncertainty and risk. But along the way I had to make some deep changes and sacrifices. I had to pack a parachute.

How did I do it? By using three principles every time, and it worked… every time.

You can use these principles to help you pack your own career transition parachute:


  1. Commitment
  2. A Plan
  3. Perseverance and Flexibility


Commitment is your willingness to make the bet on yourself. You need to believe, go all in, take measures, and pivot as needed.

Don’t let age be a factor. You know the saying that part of success is the journey? It's true. I didn't get to this field until I was 43. Honestly, I wasn't ready before then. You get where you need to go in the time that it needs to take.

But you gotta believe. Commit—to yourself, the plan, and what it will require to get to the other side.


A Plan

This is the roadmap. Take your time with this one. Women have financial challenges that are very specific to them—greater longevity, lower lifetime earnings on average, glass ceilings… the list (unfortunately) goes on. So the more effort you dedicate and the more research you do, the higher the likelihood of success. Think of the plan in two discrete parts.

The first part are the mechanics of how you get to point B. Ask yourself questions like:


  • Will it require additional credentials?

  • Do I need a mentor?

  • Can I transition over time while I am still working my regular gig?

  • Can I volunteer to build expertise that can be converted to paid work?

  • Can I get backers for a business or self-finance?

  • How long will it take to make the money I want?

The second part is how to pull it off financially. This is where the most shortcuts are taken to one’s peril. And this is exactly when women are well served to get a financial advisor to help them frame it all out. There needs to be no ambiguity here. It must be the clearest part of your strategy. Ask yourself questions like:


  • Can my new career fulfill current and future financial goals?

  • How much do those goals cost?

  • How much in savings do I need to cover my core expenses?

  • How long do I think it will take to transition?

  • What am I prepared to give up today to build a financial “war chest” to get me through the time when I have little to no income?

  • Are there ways I can lower expenses to stretch out my funds if possible?

  • Am I prepared to go into debt to do this, how, and to what degree?

  • Can I tolerate financial risks, such as needing to work longer than I’d originally planned?

Be conservative with your assumptions. Write them down. Make spreadsheets. Doodle. Record your thoughts. This makes the process tangible. Draw from your network of friends, family, co-workers, alums, people with common experiences, and professional advisors.

Perseverance and Flexibility
There will be times when things go sideways. Where there are unexpected upheavals. When plans must be modified. The question is not whether it will happen—it will. You have to game for these moments. You do that through brainstorming and scenario testing.

This is also where a good financial advisor can help you ask the right questions such as:

  • What are the conditions under which I revise my strategy, or try something else, or go back to square one?

  • What are the financial implications of each strategy?
Thinking about this in advance will help you roll with the changes.

While a career transition can feel like a very Vegas-bet-on-black move, a methodical, thoughtful approach to financial planning can take some risk off the table.

You can jump out of a career airplane if you follow these steps. But no woman is an island. Get advice. We all need help packing the parachute.

Schedule an introductory call to discuss how to pack your parachute with an advisor specializing in working with self-reliant women.