Decision-making: Packing Your Parachute

Make Life-Changing Decisions Confidently

I’ve always taken the path least traveled, and have made some drastic decisions along the way. I graduated early from high school, skipped the college track, and plunged straight into career. For my first job as a ballet dancer, I moved to a new city, found an apartment, and started from scratch at 17. A couple if years later, I was offered a job in Romania and took it. I moved there without knowing a soul in the country or more than ten words of the language. When it was no longer the right place for me, I moved back to the US. Fast forward further, and I left the only career & skill set in which I had working experience, went back to school, and changed lanes to a completely different career. 

I’ve done a lot in my short life, and I don’t imagine I’ve used up my life-changing decisions yet. In the modern workplace, many young people don’t expect to start a job with one company, work their way up the ladder, and retire with the same company. Most of us don’t even expect to spend our entire careers in the same field or sector. 

Change can be unpleasant, and most of us carry around at least a sliver of fear of the unknown. Yet the goal is not to avoid making life-altering decisions, but to make them to the best of our ability and to have a support system in place when difficulties arise. When you know your parachute is packed well, you’re not falling to your demise: you’re just landing in new terrain. 

Photo by Fertnig/iStock / Getty Images
Photo by Fertnig/iStock / Getty Images

1. Gather Information

Whenever there’s a new opportunity or a reason to consider new paths, the first and most important part of making a decision is learning as much as possible. When information cannot simply be researched, asking questions becomes paramount. Early on, I thought that asking questions would give away my inexperience and give others a reason to reconsider the opportunities they offered. But more often than not, people expect to be asked questions and are happy to fill in the blanks. I’ve learned to ask as many questions as necessary until I feel satisfied that I have the whole picture. Lack of knowledge or experience are not reasons to be embarrassed. Having a clear understanding of options, possible benefits, and repercussions is more important than pride. 

2. Re-Visit Your Goals

Once you know what you’re dealing with, set aside decision-making and think about your goals. Keep in mind short-term goals, as well as long-term. What do you need in order to be a happy, healthy, fulfilled person? What would you like to improve? What do you want to accomplish both now and over your lifetime? In my case, it has always been easier to separate the decision from these questions before coming back to it. After I’ve reevaluated my goals, I go back and plug each of my options into a “what-if” scenario. If I can’t see something fitting in with my goals, the decision is easily made. 

3. Ask Advice

Find people you trust, and ask their opinion. You don't have to take their advice, but they may see the situation differently and have valuable insight to contribute. Experts or those with experience in similar situations are invaluable when gathering information and asking advice. At the end of the day, no one is going to make up your mind for you, so don’t be afraid to hear other voices on the subject. 

3. Organize Thoughts & Feelings

I am a list-maker. I make to-do lists, grocery lists, task lists, lists of interests, lists of places I want to travel… I could go on (and on). It always helps me to see information concisely summarized in a list. When trying to make decisions, I will write down my options, the pros and cons, and details that affect my decision. The option with the longest list of pros or shortest list of cons may still not “win,” but it at least gives me space to have a comprehensive look at the possibilities. 

4. Consider Alternatives

When a boss offers a promotion, it is so tempting to see the options as “A” and “B”. Either A) I take the promotion or B) I don’t. But what if you’re not looking at all of the possibilities? What if the promotion isn’t the direction you want to go, but being stuck where you are isn’t appealing either? Is there a third option? Could you look for a job elsewhere, or negotiate for advancement in a direction in which you ARE interested? It is too easy to get stuck choosing between the options in front of us without looking beyond them for better alternatives. Life is full of infinite possibilities; it may just take some creativity to see them. 

5. Sleep On It

There may be circumstances that require immediate action, and therefore an immediate decision, but whenever possible, take some time to evaluate and synthesize the options. I find it extraordinarily helpful to spend some time actively thinking about the choice. This includes time looking up information, evaluating long and short-term goals, and making lists. After spending a couple of hours I usually feel overwhelmed both with information and with the weight of the decision. At that point I purposefully get up and walk away from it. I find something else to occupy my mind. Allowing oneself the time to not think about a decision can be just as important as the time spent actively engaged. After taking a break, and thinking about other things, I always come back with a clearer mind and a calmer attitude. It's giving the chaos of churning thoughts a chance to settle in order to sift through them methodically. If possible, allow a good night’s rest and come back to it in the morning. 

6. Trust Your Instincts

Our hearts and our heads deserve more trust than they’re often allowed. If one option just doesn’t feel right, there’s probably a reason. Even if something looks great on paper, it can still be the wrong decision for you. Don’t disregard your emotional opinion or intuition. Quieting that murmur in the back of your head, or ignoring that sinking feeling in the pit of your stomach is discounting part of yourself. Trust that you know what you want and what’s best for you, even if you can’t pinpoint it logically. 

7. Don’t Look Back

Don’t continually ask yourself if you made the “right” decision. What’s right for you may not be the same thing that’s right for everyone else. You only need to know that it was the right choice FOR YOU. Have faith in yourself, and don’t second-guess. We all make the best decisions we can with the knowledge and experience available to us. Mistakes are part of life and hindsight is 20/20. That’s a formidable combination, but the potential of making a mistake cannot be allowed to become a paralyzing force. Forcing yourself to own the decision and have confidence in your own judgment will make it much easier to follow through with the actions necessary to affect change.

8. Surround Yourself with Supporters

Changing your trajectory involves going against the current momentum. This can be difficult, painful even. An important part of big change is having the right support. It is much easier to get up again after failure, knowing there are people who still believe in you and love you. Knowing that I will never be truly alone has allowed me to take calculated risks, and enjoy the payoff of success. I live a truly charmed life, not because I haven’t had to work hard or struggle, but because I know that even when I fall miserably short, I will still be loved. Find people who will always be on your team, and you’ll never truly fail. 


Once you’ve methodically considered, and you’ve got support for when things get rough, the decisions become easier. Even the toughest decisions become bearable. When there are no clear answers, remember life is never black and white. We’re all doing the best we can, and there’s no shame in giving it your best shot even if it doesn’t work out in the end.