How to Prepare for Your Career’s Second Act

Dear A.S.,

I love questions like this one – the chance to think creatively and brainstorm “what could be” without the stress of having to do something right now. I get this question quite a bit in my coaching activities. People also often reach out to me from the industry to talk about where they could go and what they could do next. The old concept of retirement – where you play golf and pickleball – is not that appealing to many people in our industry who have enjoyed contributing and making a difference. But, like you, they don’t necessarily want the pressure of managing people and having to worry about the markets on a daily basis!

I have some suggestions to start thinking about what you could do in another three years when you have more latitude and less financial responsibility:

1. Consider what you enjoy about what you do now. I hear that you want to leave the industry, but what about your role or your career have you enjoyed? Try and parse out specifically what elements of the journey have brought you joy. For most of us, there are stressors, but there are also aspects which energize us. Without being industry specific, make a list of what these things are – those are your transferable interests and skills.

2. Identify industries that do interest you. It can be difficult to make a transition. However, for senior level people who have done a lot in their careers, it’s a little less challenging. Your skills in management, leadership and change management are valuable no matter what industry you choose. Embark on a process to learn about other industries and see what’s of interest. Talk to friends and friends of friends on an informational basis. Grab coffee or lunch with people who are doing something completely different to learn more about what their industry needs for skill sets. Learn the jargon and areas of focus.

3. Think about anything you enjoy doing, such as a hobby or volunteer effort, that could be turned into a part-time or full-time job. We do animal rescue in our home and have for many, many years. When my kids first wanted to make money, two of the three set up dog-walking and cat/dog sitting businesses. It was amazing the amount of money they could make doing this on a weekly basis! One of my son’s friends is a photographer and learned how to use his drone to help send pictures for a large organization that needed aerial views.

One of my colleagues left a white-collar job while in his 50s and started his own landscaping company. He’s always been a gardener, and his company focuses on exotic plants for high-end homes. Another colleague left our industry and set up a yoga studio. She is doing about 30 hours there and volunteering at a local homeless shelter for another five to 10 hours. She is ready to hire a couple of additional yoga teachers to free up even more time! The possibilities are endless. Take some time to think about what’s meaningful and interesting to you if not another similar career in a different industry.

4. You could also start doing something now that could lead to an off-ramp in three years or so. One of my advisor clients always wanted to do stand-up comedy and as we talked about his retirement, we realized he could start doing shows on weekends and evenings. There was no reason to wait until he was ready to leave his firm. He was able to continue to run the firm successfully, implement a clear succession strategy and explore his passion all at the same time!

You don’t need to wait until the magical three-year date. If you do, you might become depressed three years from now when you realize you haven’t made plans. Start exploring, considering, and learning now so you are prepared when you decide to make a change. You might even find reason to do something before the three years are up, but at least you won’t feel pressured to do so until you are ready.

Dear Bev,

We are just past the mid-year point and our team has not implemented either of the major projects we all agreed to (new CRM, client segmentation process). We know what we need to do, but the team isn’t doing it. I keep telling them they need to be more proactive and not wait for direction, but I am starting to think I haven’t hired people who know what to do without my prodding and pushing. How do I ensure these important things are in place by the end of 2024 without me being the one to play project manager?

K.C.

Dear K.C.,

Your note is one I receive a lot – it’s is initially about the frustration of something not happening within a financial firm (large or small), but somehow it segues into the team being the problem. They are reactive, not cooperative, not engaged and so on. These are often two separate discussions, so I am going to address your need for implementation before the end of this year.

Please consider using the SHIFT process I have written about several times before in this column. I have used it with hu hundreds of teams to help them implement new ideas or create change. Even if you can implement the first three steps, your team likely needs a bit of support, planning and direction. Accusing them of simply waiting for direction is probably unfair. It is often incumbent on the leader to create a direction and then allow people to implement accordingly.

S- Specify the desired outcome. Make sure it is clear what “implementing the new CRM” or “implementing new client segmentation” really looks like. Yes, I know what both mean at a high level, but what does it mean for your firm? Are you transitioning from an existing system? Needing to do clean-up of data? Having to communicate with clients on the new segments? The two original action items sound clear, but there are many aspects that might need to be clarified and defined. Make sure this has been done.

H – Highlight the obstacles and categorize. What is getting in the way of taking the necessary steps? Allow your team to share where they are getting stuck, what’s unclear or where they need resources. Categorize what they can control, what they can influence and what’s out of their control. Focus them on overcoming the obstacles. Provide space for them to do this.

I – Identify the human factor. Who should be involved in these efforts? What roles should they play? Who needs to communicate with whom? What skills are required. This part is critical because often we expect things out of people who may not have the skills, knowledge or interest.

F – Find alternatives. What options does your team have to get these things done? Help them to brainstorm how they can make progress while also doing the work of the day-to-day.

T – Take disciplined action. Perhaps my favorite. Do you have a plan – discreet “chunked” steps with timelines and assigned accountabilities that show each and every person what they need to do, and when?

Please don’t assume your team is incapable or not proactive without giving them a chance to organize around getting these things done. If they don’t make progress after this, you may have to consider whether you are asking something they are incapable of doing.

Beverly Flaxington co-founded The Collaborative, a consulting firm devoted to business building for the financial services industry, in 1995. The firm also founded and manages the Advisors Sales Academy. The firm has won the Wealthbriefing WealthTech award for Best Training Solution for 2022, 2023 and 2024. Beverly is currently an adjunct professor at Suffolk University teaching undergraduate and graduate students Entrepreneurship and Leading Teams. She is a Certified Professional Behavioral Analyst (CPBA) and Certified Professional Values Analyst (CPVA).

She has spent over 25 years in the investment industry and has been featured in Selling Power Magazine and quoted in hundreds of media outlets, including The Wall Street Journal, MSNBC.com, Investment News and Solutions Magazine for the FPA. She speaks frequently at investment industry conferences and is a speaker for the CFA Institute.

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