Planning for a Second Act + a sabbatical

Hello friends and welcome back to another edition of my newsletter, where I share lessons and tips around entrepreneurship, finance, and life design.

Before we get to today's newsletter, here’s some of the content I’m consuming that you might find interesting.

What I’m consuming

I recently shared this song with my team. It’s called “Get Up” and it’s by Shinedown. It’s a very motivational piece of music and works great mixed into a workout playlist or a morning routine. Give it a listen and let me know what you think.

I’m fifty years old today.

The big 5-0.

Outside of more gray hairs and a few extra wrinkles, I don’t feel fifty-years-old. At least not mentally. Sure, I have more aches and pains these days, but I don’t even feel fifty physically. I’m probably in the second-best shape of my life thanks to lots of body weight exercises, pull-ups are an amazing full upper body workout, and yoga. My best shape being when I was in my early twenties and a professional martial artist.

It hit me the other day that I don’t have a lot of professional time left in front of me. I suspect, if all goes well, I have 5-10 years of work left. At least, that is my goal.

That means it is time to ask if I have accomplished everything I want to in my career. I don’t think I’m quite there, but I’m close. I’ve been honored to chalk up quite a few accomplishments, including a career trajectory that has taken me pretty high up the corporate ladder.

The one place I feel like I haven’t accomplished everything I wanted to professionally is in my entrepreneurial endeavors. I’ve been able to grow a few small businesses, but I’ve never been able to scale anything beyond a nice side hustle. Some of that is on me for bouncing between business models for the past decade or more.

My challenge has been that I have such an eclectic background (finance, marketing, product management, strategy) that there are multiple business models that work for me. Plus, I suffer from shiny object syndrome like most entrepreneurs. Most of my revenue comes from one of two places - my courses or writing business plans for people seeking SBA loans. On top of that, the business models that work best for me in terms of revenue often aren’t the models I enjoy the most.

All of the above has led to a 10+ year battle of bouncing between business models.

I recently explored hiring a branding coach to help me boil everything down into one model, instead of the 5+ websites I have. But, they were either grossly expensive or I didn’t feel like they were paying attention to what I was asking for.

Then, on Thursday, I had a realization while driving our daughter to school.

I’ve also thought that I had to grow my businesses to a) allow me to escape the corporate world; b) be able to sell the business. I felt compelled to do that for two reasons - 1) because I wanted to prove I could do it and 2) for the financial benefits.

Then I realized, I don’t have to grow a business to the point of allowing me to quit my day job. I’m one of the rare people I know who has a day job that is more than tolerable on most days and even rewarding on others. I work with a great group of people and I earn a very comfortable livelihood. That could change, but right now I have the best of both worlds.

What’s happened is that I relearned a lesson that I uncovered while writing “The Ladder or The Grind.”

I’m starting to realize that I have things set up pretty well to focus on one business model once I retire from my day job. Some people call that your Second Act and I think that is fitting. So, instead of feeling the pressure to consistently be grinding away at growing my own business, I’m focusing on putting things in place that will allow me to have a great Second Act.

In the meantime, I get to scratch my entrepreneurial itch, without the pressure of growing for growth’s sake.

I’d encourage you to explore this Second Act principle.

What does that look like for you down the road and what are the skills that you can focus on learning in your current professional environment that enable you to get that well?

I’d love to hear your thoughts. Hit reply and let me know what your Second Act could be.

A Summer Sabbatical

My calendar always has two periods blocked off on it where I take a sabbatical from my side hustles. The winter sabbatical rounds from November 15th to January 15th. The summer sabbatical runs from May 15th to July 15th.

In the past, I haven’t been the best at sticking to my hustle sabbaticals. I’m hoping I can do better this time around. My good friend and co-worker Stephen is taking a month-long sabbatical from work and he will be spending it in his home country of Scotland and England.

That has me motivated to take a good long break myself.

So, I’ll not only be taking a few weeks away from work, as well as a break from business.

All that is to say, if things are a little quiet from me for a while, you will know why.

I’ll see you on the other side.

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Read past issues

Jun 15
Go-to-Market Made Easy: Your Roadmap to Customer Acquisition
May 24
Planning for a Second Act + a sabbatical
May 05
This isn't 2008. But, it's not that much better
Apr 20
Market Whisperer: Knowing Your Customer Better Than Investors
Apr 14
Energized > Rested
Apr 07
Numb the pain, silence the teacher
Mar 31
The Myth of the Big Exit
Mar 23
Growth Gears: Equity vs. Debt - Fueling a Startup’s Journey
Mar 16
A candid conversation about fear
Mar 09
The Technical Product Managers Guide to Go-to-Market
Mar 03
My goal was 100 financial plans. I did 10x that goal.
Feb 25
Poor MVP, no one likes you
Feb 24
Beyond Bytes: Why Interpersonal Skills are the New Power Tools for Success
Feb 17
This one question changed how I looked at contingency plans
Feb 10
From $100k -> $75M - this week's fundraising lessons
Jan 27
The next big finance opportunity
Jan 20
This is how long a startup funding round lasts
Jan 09
How I'd market a loan broker business
Jan 02
25+ years of finance experience in less than 5 minutes
Dec 28
How to have a stress-free relationship with money
Dec 17
How to buy a business with little money down
Dec 12
Want to 10x your business? Try the strategy that most people fear.
Dec 05
Why being loan-specific as a loan broker is best
Nov 28
The Power of Micro Markets
Nov 19
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Lessons from acquisitions
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My business plan cheat code
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Sep 11
What I’ve learned as a startup analyst for an angel investing syndicate
Jun 24
My favorite economic analysis tools
May 29
Which SBA Loan Has the Lowest Down Payment?
May 01
The Power of a Decision Matrix
Apr 24
Things to consider when buying a business
Apr 17
Buy a Business vs. Start One
Mar 31
How do Micro SBA Loans work?
Mar 03
Common Investor Term Sheet Components
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Thoughts on <my first Angel Investment>
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There Are Two Main Types of Business Plans
Dec 09
The Best Pitch Deck Templates