Circumstances are always changing in life – new jobs, moving, the birth of a child, getting close to retirement, job promotions, unplanned changes like losing a loved one. Most of these changes require planning or re-evaluating your financial situation. Or maybe you are dreaming of some of these changes in the future and waiting for your finances to allow you to move forward with the next phase of life. Many times you hear people say, “I can’t have a baby, get married, or retire until I have this amount of money.” Sometimes this is true, but other times you might not even have a goal or end in mind. This makes it hard to feel confident and comfortable going through with the next milestone. Other times you might just want someone else to tell you, “You have enough money, and you can do this now!”

Navigating the different transitions and milestones

Changing careers

If you are considering a career change, there are so many factors to think about. The first thing to ask yourself is “why”. Why are you considering a career change? Are you wanting to change jobs to align more with your giftings and passions, or wanting to put yourself in a better financial position? Both of these ambitions are wonderful, and hopefully they coincide with each other – getting a higher paying job doing what you love. Sometimes, however, this is not the case, and to pursue meaningful work you have to take a pay cut. You might even have to save up to take classes or go back to school to obtain the skills you need. If this is the case, then reviewing your budget and cutting spending and costs wherever possible is going to help you. If you are considering changing careers, it might be wise to hire a life coach or someone that can help you navigate your path forward toward reaching your goals. Another thing to consider when switching jobs is rolling over your old 401k. Here is a blog on how to do that. If you want someone to help you choose investments and manage your 401k, then you should talk to a financial advisor. If you are considering two different job opportunities, an advisor can even help you to weigh your options including the benefits and pay structure.

Getting married

Getting married to the person you love and want to spend the rest of your life with is such an exciting time. As you plan and prepare during your engagement period some things to discuss include: What are your 3-5 year goals? What are your long-term goals? Do you plan to have kids? If so, when? How do you individually handle money now and how will you handle money together in the future?
This last question is a big one as you’ve all heard it said that one of the main reasons couples fight has to do with money. Check out our blog titled, “Marriage and Money.” You also might find it helpful to learn about each other’s relationship with money and you can learn about which money psychology you each struggle with most, with our blog titled, “Money Psychology.” Other financial questions to discuss are:

  1. Do you have a budget?
  2. Do you have savings?
  3. What are your 3-5 year goals? (Personal and financial goals)
  4. Are you saving for a house?
  5. Do you have any debt? If so, how do you plan to tackle that debt together?
  6. Do you have a 401k?
  7. Do you have a retirement plan?

When getting married, two major ways you can set yourself up for success are:

1. Find a counselor – someone that can help you walk through these questions and ones you haven’t even thought about yet.
2. Create a financial plan – you can download our “Investor’s guide to your first $100,000”, which helps you set goals and address the different checkpoints toward your financial freedom.

Having a child

Having a baby is such a joyous occasion, but with this big change comes huge responsibility including a major change in the way you spend your time and money with another person to clothe, feed, and provide for. This might even mean re-evaluating your job and deciding for one parent to stay at home and quit their job or change jobs so that one parent can work from home. If you are considering quitting your job, this might come with a big pay cut, and that is something you want to plan and account for. Do you plan to hire a nanny? Or, do you plan to pay for childcare? These are questions that are part of the equation on what is best for you and your family. You will need to spend some time adjusting your budget to account for the changes you plan to implement.

Becoming an empty nester

When your youngest child goes off to college, there are so many mixed emotions. You might be asking, “What do we do with all this free time?” now that you are not running kids everywhere, or watching their events and performances. For so long your life has revolved around the responsibility of caring for your children. As they move out and less of your time revolves around your kids wants and needs, it will take some planning and adjusting to reevaluate how you spend your time.

You have done your job–you have set them up for success as a responsible and capable adult as best as you could, and now you have to let them soar on their own. It can be an emotional experience since they have lived with you for the last 18 years. When your last child moves out, you have to reevaluate what is next, especially since you have more free time to pursue some core pursuits or hobbies. Maybe you have had a few things you have put on a shelf and forgot about, and now is the time to dust them off and reconnect to some of your old passions. Or, you might have a new hobby you want to try. The sky’s the limit and it is super important to spend some time alone reflecting on this new season, or if you are married to have a conversation with your spouse about your fears, concerns, hopes, and dreams for this new milestone and transition. Just make sure you are being intentional with your extra time and set goals and align the way you spend your day with the goals you have created for yourself, or as a couple.

Here is a helpful time tool –

“How we spend our days is of course how we spend our lives,” -Annie Dillard.

First, decide the categories that make up the way you spend your time throughout a 24-hour period. Some examples are below. Then decide how much time you spend on each category. If you are not aware of how much you spend on certain areas such as distractions, you can pay attention throughout one 24-hour period and create a log to get an idea.

  • Paid work
  • Passion work (side projects, hobbies, core pursuits)
  • Professional development (business development, networking, job applications)
  • Personal development (journaling, classes or workshops, inspiring reading)
  • Relationships (spending time with family, phone calls with friends, dates)
  • Play (enjoying nature, shopping, casual reading, going out)
  • Wellness (working out, taking necessary breaks, self-care, therapy)
  • Support work (volunteering, mentoring)
  • Distractions (social media, TV, taking extra time to get out of bed in the morning,)
  • Maintenance (running errands, getting ready, doing chores)
  • Cooking
  • Sleeping

Once you have an idea of the amount of time you spend in each category, you can create a pie chart filling in each section based on the number of hours spent. When you visually see how you spend your time it will then lead you to evaluate and make changes to align the way you spend your time with your short and long-term goals.


As you move toward retirement, you may start wondering if you’ll have enough money. However, the best time to ask that question is well before you announce the end of your 9 to 5 life. Long before you file with the Social Security Administration, consider hiring a financial advisor who can help you navigate the complexities of monthly benefits and make sure you get the most money possible. They can also help you identify opportunities to give back and work with you to prepare your financial legacy.

In addition to the financial complexities of retirement, there are so many other questions for you to ask yourself and consider:

  1. What is my purpose and how can I pursue this in my retirement years?
  2. Where will I live? Will I stay where I am, downsize, or relocate to live in a place I’ve always wanted to live or live closer to family and friends?
  3. What core pursuits will I pursue?
  4. How will I spend my time?
  5. What bucket list items do I plan to check off my list this year?
  6. How will I be generous with my time and money?
  7. Who are the people I will choose to spend my time with?
  8. What is the legacy I want to leave?
  9. Will I go back to work doing something else I love to do?

Let your money work for you. We want to help you live the life you have always wanted. At Goodwin Investment Advisory, we truly care about YOU and want to create a financial plan that is individualized just for you, your lifestyle, and your situation. We want to give you the confidence that your money is invested right and will be there when you need it. We would love to connect with you, hear your story, and see how we can help guide you in your financial journey and to help you reach your goals through all your milestones and transitions.

This document is intended to stimulate thought and discussion, and is not intended to be an exhaustive guide on the topic. The content is shared based on our experience, but your situation may be different, and may require a different approach. Please contact your GIA advisor to discuss any questions you may have, or consult with professional coaches / counselors regarding your career and relationships.
By Published On: September 15th, 2022

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About the Author: Tara Bruce

Tara Bruce
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