Making a Smart Career Transition

Do you catch yourself daydreaming? I get the sense there are a lot of you out there who are looking for something different in your work life. It could be a sense of burnout, feeling a lack of purpose or meaning in your day-to-day activities, or not having the same interests and energy you had earlier in life. Specifically, you could be yearning for more flexibility in your schedule, like taking off to your grandchildren’s sports events or getting more time to visit interesting places.

Changing careers is a lot like remodeling your home while still living in it. You can't just knock down walls and hope for the best—you need a blueprint. Tanya and I went through this starting in 2022, when I began dreaming of something other than a career in technology. I’ve thought back to those times; the dreaming, the preparation, and the decisions, and wanted to spend time sharing what I learned with the hope it helps you move towards the life you want to live. I know I’m laying this out linearly, but in reality, a lot of these ideas overlap.

Align at Home

Make sure you and your spouse are together on the direction. This will probably take many conversations as your thinking matures. Ask each other:

• Why are we pursuing this change?

• What are we willing to sacrifice (temporarily or long-term) to make it happen?

This isn't a one-time talk—it’s a recurring conversation throughout the ride, especially as new opportunities, choices, or challenges show up. Alignment means you’ll have more staying power when you question your decisions or encounter stress.

Explore Directions

This is where you align your head and your heart by investigating possibilities. You can follow this framework:

1. List out your skills, interests, and the things you care about most. Lean into what gets you pumped and produce a set of solid options. You might consider some sort of career assessment to gain clarity.

2. Have a conversation with several folks already doing what you think you might want to do to learn what they do day to day, in REALITY.

3. Find opportunities to try out a job before jumping headlong into it. For instance, what if you think you want to be a teacher? While you continue in your current job, try tutoring one student to get a feel for it.

Often, your head will talk you out of a possibility before you start exploring, while your heart will be saying yes! Don’t worry about the financials at this point, unless you’re choosing underwater basket weaving. Resist the urge to rule anything out yet. Wait until you have more information.

Construct Your Runway

Making a move takes time. The good news is that you don’t have to sit around waiting. Be proactive in several ways to step over the rocks and crevices on the trail instead of launching yourself off a ramp over the great divide like Evel Knievel. Here are suggestions to get ready:

• Build a fund to bridge your transition. A career change, especially to a completely new industry, likely involves at least a temporary pay cut. Depending on the level of financial sacrifice you are willing to make and the reality of life’s expenses, having a bridge fund of 6-12 months of expenses cushions the change. You can build this by simulating a lower income now and saving the difference, or increasing income with a side hustle. This money isn’t meant to be invested, so sock it away in a high-yield savings account.

• Gain knowledge in your chosen path. Don’t wait to start learning what you need to know. This could be attending seminars, taking classes at the community college, or listening to podcasts. These activities might result in a certificate demonstrating a base level of competence or a license you need to practice (e.g., real estate or financial services). They also probably cost money. Avoid allowing urgency to drive you towards using a loan or your credit card. Wait until you have the cash. Don’t shoot yourself in the foot with this one!

• Join a community of people who are talking about and doing the work you want. Various industries have associations you can join and groups that meet regularly for education and connection. Social Media has nearly limitless numbers of groups you can participate with.

Land the Role

Take your time searching for the right fit and don’t jump until you are ready. Avoid FOMO and taking the first opportunity, unless it's the right one. Sometimes your emotions can get the best of you because you just want to be done with your current situation, and you think other options won’t materialize. Here are some signs that it’s the right role:

• You’ve got your blueprint in order, and you’re on the same page with your spouse.

• The role has a clear, intentional path —from entry level to the rung on the ladder you want to reach. This includes the salary you want to be making in the long run and the training you need to succeed.

• The financial numbers work: Don’t finance the transition with debt or go without essentials like health insurance. Maybe the right fit coincides with a spouse going back to work, so you have other health insurance options, or they reach a certain point in their career that comes with more income.

A quick note on finding opportunities. I strongly encourage you to find openings via relationships you already have. This contrasts with blasting your resume to three employers daily, which has the appearance of activity, but with little realistic chance of working. Blasting resumes has the real risk of derailing you from moving forward because of discouragement. Rely on telling anyone and everyone you know what you’re doing, and don’t be shy about asking them to “put in a good word” for you.

You Found the Role, Now What?

It really is amazing to see what can happen when you take your time and find the right fit. Here are some things to consider as you get up and running in your new path.

• Be an apprentice. You built expertise in your previous career over many years, and to get where you want to go in this new path, you will likely need to develop your chops in a whole new set of knowledge and wisdom. Soak up as much information as you can, make the most of every reasonable opportunity given to you, and dare to make mistakes!

• Take time to adjust. Transitioning to a new field may come with changes in routine, work culture, and responsibilities. Career transitions are emotional. There will be days when you feel energized and days when you question everything. That’s normal!

• Remind yourself where you are going. It can be tempting to get impatient with the process. Remember, this might just be the first step in the new direction. At this stage, I found reassurance, reminding myself of the blueprint Tanya and I laid out, and saw that we were on course in terms of income and the type of work I expected. After six to twelve months, are you where you thought you would be? If not, what adjustments, if any, need to be made?

---

Ready to Design Your Second Act?

A career transition doesn’t have to be a leap into the unknown. You just need to build the right structure underneath the dream. At The Dala Group, we love to have conversations about your vision of where you want to go. And if you’re not sure, we’ll walk with you as you unearth the why you want to pursue. And most importantly, we’ll help you assess your current financial situation and present financial moves to make to set yourself up in the short term to get there and understand the impact that has on your financial horizon. If you’re ready for a conversation, schedule an intro call.