Last September, I wrote a blog post with some “Barbservations” about entrepreneurship during a pandemic. In that post, I described five personal learning lessons: Be visible on social media, do some pro bono work, get a video-conferencing license, say “no” to bad-fit assignments, and chart a new path.

After decades working in academia, I have now been a full-time financial education entrepreneur for 15 months. Since I have had few role models for how to do this, I have built many bridges as I crossed them. 

I can count on one hand the number of colleagues I know who left longtime careers and continue to work actively in the same field.

In an effort to help other aspiring third-age entrepreneurs, below are 10 additional learning lessons:

1. Show Up

Fewer people think I am “retired” now than when I first left Rutgers University because I made very conscientious decisions to attend conferences, present webinars and podcasts, respond to media queries, “work out loud,” and share content via social media.

I smiled recently when a colleague said “you’re everywhere” because it indicated my strategy was working. 

Branding, maintaining visibility, and professional development are ongoing processes for all successful entrepreneurs to attend to and are also great antidotes for older adult ageism.

2. Identify Deliverable Stages and Invoice Accordingly

I did not do this with one large project that extended for six months. There were multiple levels of review that took much more time than either the client that hired me or I ever anticipated.

Now I set specific project milestones for clients with a first draft of content being the first deliverable that I invoice for. 

This strategy evens out cash flow and makes income tax planning easier.

3. Understand the Client’s Funder

Clients receive external funding to hire me for some of my work projects. Thus, it is key to understand their funder’s requirements and “hot buttons” (e.g. certain topics and/or website links to avoid).

Also, accept the fact that projects take longer when more entities are involved and that some funders hold back the money for your client to pay you with until they approve the final project results.

4. Think Twice About Public Entities 

I am very wary now of doing any future work for state governments and public colleges.

Their hiring and payment “systems” are simply too onerous and time-consuming for this solo practitioner (e.g., proving my U.S. citizenship, filing an out-of-state business registration, completing elaborate online forms, and undergoing a background check that required unfreezing my credit, which I did not do).

My advice: Ask plenty of process questions when someone from the public sector wants to hire you.

5. Get Project Details in Writing

On the other side of the spectrum are clients who do not have any paperwork or hiring process at all.

In this case, I provide a simple one-page memorandum of understanding (MOU) that includes a complete description of the deliverable, deliverable milestones (e.g., first draft, first round of revisions, final draft), the project timeline, and the amount that I am charging per hour and in total for the project.

6. Stick to Your Niche

My niche is writing, speaking, and reviewing personal finance content. Period. 

I said “no” to requests to conduct research, write grants, and do a curriculum bias review, for which I was not qualified by training or life experience. I also passed on a speaking opportunity because I am not ready to travel by air yet.

7. “Bookend” Your Day

Much has been written over the past year about “blurred boundaries” with so many people working from home.

As a solo entrepreneur, it was quite a change for me from working with others at an office. I exercise before and after work hours to establish boundaries for when my workday starts and ends.

8. Fill Work Spaces

I have had almost no project down time since January 2020 because I have one ongoing client as an “anchor.” 

With ad hoc projects, as soon as I finish one, I immediately start another in my queue to create space for new projects that may come along. 

I fill small time gaps binge-writing posts like this one.

9. Monitor Income Tax Payments

With the exception of the “anchor” client, my first-year income as an entrepreneur was a big unknown at the start of 2020. 

By December, I had doubled revenue expectations. I used previous tax returns, the IRS tax withholding estimator tool, and the safe harbor rule to avoid under-withholding.

10. Create Synergies

Several client projects involve creating content for professionals who serve military families. I found that research and learning curves that informed one project also benefited another. 

Similarly, I created a number of templates (e.g., for invoices, MOUs, and online quizzes) that can be used across multiple projects.

As I wrote in my recent book, Flipping a Switch, everyone needs some “big rocks” (e.g., work, volunteerism, caregiving, socialization) in their day to provide structure and a sense of purpose. 

Entrepreneurship is one of my “big rocks” and provides fulfillment, an outlet for creativity, and a good income. I hope that my insights are useful.

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