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Starting a Business (or Side Hustle) from the Inside Out

By Kim Neumann October 23, 2023 Managing Money

Can your new business be a source of income and joy?

A space for your values, talents and creativity to shine?

I’m a firm believer in doing what you love.

Especially when it comes to starting a business (or side hustle).

After all, time is precious. And I don’t know about you, but if I’m going to spend 20, 30 or 40+ hours a week on a business or side hustle, I’d like an astronomical ROI: in dollars, mental stimulation, creative satisfaction, and the warm fuzzies I get from helping people out.

I want the package deal. How about you?

So instead of launching the 22,038th print-on-demand t-shirt business (not that there’s anything wrong with that), let’s look at the rich tapestry of your life experiences, passions, and latent insights that hold the key to your fabulous new enterprise.

And that, my friends, leads us to the following little exercise, designed to help you start a business from the inside out.

This process focuses on 5 areas of inquiry: Experiences, Expertise, Opportunities, Preferences, and Need.

Related: Would You Set Up A New Business in Your 60s?

Ready, Set…

Before we dive in, please choose a format for completing this exercise.

The format I find most helpful is a simple alphanumeric nested list in Google docs. This makes the entire document scannable (and if you’re anything like me, it will get looong). You can go as deep as you wish with related bullet points. Alternatively, you can write it all out, journal style. A paper and pen approach can offer a nice, relaxed pace. Add a hot mug of tea or other favorite beverage to really set the tone.

I’ll include this nested list example in our first area of inquiry, Experiences.


First, list your work experiences. Kind of like a resume, you’ll list what you did, when/how long, and your role. Include what you enjoyed, what you learned, what you struggled with. Any lessons, gifts, takeaways from that experience?

Repeat the process for other types of experiences: hobbies, events, projects, a daily ritual or routine you enjoy, special interests, and so on.

Here’s the nested list format I like to use:

For me, it starts with my current work (running my own marketing consultancy) and mentions everything from being an au pair in Paris at age 20 to my temp job at Pixar when I first moved to California. It touches on areas of importance to me including health & fitness, writing (an early passion fostered by my 3rd grade teacher, Mrs. Brown), and my morning routine where I dedicate the wee early hours to meditation, journaling and creative expression.

By touching on these varied life experiences, you’ll see them in a more objective light, while revisiting or rediscovering their meaning for you.


Next, we explore your special talents and expertise.

What do you consider yourself to be an “expert” at or – modesty aside, please – better at than the average, ordinary citizen?

It could be that you’re an amateur photographer, but your expertise is with people. You just have a knack for getting them to feel good in their skin, and then, snap! You capture their gorgeous, natural smile, just like that.

Continue with the same format for Expertise, including sub-bullets for any insights that come up. Our photographer example might look like this:

    As in this example, I like to get specific with details (including names of people and what was said), to make it all the more real and rich. You can also list a talent/expertise more than once as I did, to focus on a specific aspect of it. Remember to keep the process “loosely organized” and just let the thoughts flow.


    Once you’ve exhausted your areas of expertise (sorry, is this exhausting? :) ), it’s time to look at opportunities.

    What are you good at? Who out there could use your services/products?

    Here’s a fill-in-the-blank to try:

    I’m really good at [this area of business/life or solving this specific problem] and [this kind of business or person] really needs [my product or service].

    For example:

    “I’m really good at helping people feel comfortable in their skin and then capturing them at the most beautiful natural settings in Marin County. Parents who want holiday card photos and small business owners who want updated headshots really need my no-fuss, all-fun photo services.”

    Continue to brainstorm ideas and write them down.

    Feelings are the key ingredients to starting a business from the inside out.

    It’s not the time to judge or assess your ideas. Instead, notice how you feel as they come up. Do you feel excited? Get butterflies? Remember (or better yet, jot down) these feelings – they are the key ingredients to starting a business from the inside out.

    For Opportunities, you can veer off the numbered list and just write these down, i.e.:

    On the topic of feelings… here’s a little something to keep in your back pocket, should you ever need it: How to Stay Motivated in Business Even When You Want to Give Up. (A miracle what a few moments of quiet reflection can do!)


    Preferences are a product of your values and your experiences. Being value-driven is a very good thing. Not wanting to repeat undesired experiences? That’s also a very good thing!

    So… what are your values, your life essentials?

    Your values get to have a big, strong say in what you do for a living.

    For me, my values are a no-brainer: freedom, flexibility and creative expression top the list.

    Freedom means no office, no commute, no boss. Flexibility means time is mine to play with, to schedule; it means I can put in 2 hours a day or 10, and that I’m always able to make it to my son’s school events. Creative expression is what lights my fire – it ignites my writing, my consulting, my digital products; it’s getting paid for what I love to do.

    And guess what? Starting your business from the inside out means your nearest and dearest values get to have a big say in what you do for a living.

    The other side of the Preferences coin, is of course, knowing what you DON’T want to do. Shoutout to Shari for bringing up this excellent point in her comment from Are You a Failed Retiree?

    What do you NOT want to do? For example:

    I prefer NOT to sell physical products since this requires lots of customer service, shipping headaches, maintaining an Amazon store, requesting reviews, and dealing with returns. This business model is also not aligned with my zero-waste lifestyle.

    The more you can articulate your preferences and reasons for them, the more conviction you’ll have when choices have to be made later.

    A little share from me: The example above is mostly pretty true for me (though I’m not even remotely zero-waste, but I’m trying). Yet, I still get cool ideas for physical products all the time. Then I remember my conviction for what I DON’T want to deal with. Think of these as your core value reminders to save you from unnecessary detours down the road.

    And yes, you could offload unwanted tasks to a freelancer. Just keep in mind that you now need to manage that freelancer. If one of your values is “keeping it simple,” managing someone else might add layers of unwanted complexity.

    Write all the things you DON’T want to do and why. Get as specific as possible.

    The format could look like this:


    Finally, we reach the end!

    But first, do you have a business idea or two that feels inspiring, exciting?

    If not, just work with the most potent interests or sparks. “Something with photography,” for example.

    Picture yourself doing that activity – where are you, who are you with? See what comes to mind. Allow yourself to brainstorm. Allow any and every idea to come to the surface, and write them all down.

    You may also find it helpful to review your notes and highlight the parts that stand out.

    Once you have an idea or two, let’s explore Need.

    Is there a big enough market/need? Is your market too narrow?

    Work through the idea and explore angles to find a happy medium where your inside-out business idea meets a big enough need.

    Maybe that passion for photography makes your heart skip a beat. Let’s riff on that a bit:

    Lots of business owners here need to update their headshots. Hundreds (thousands?) of families in my town/surrounding area need photos for their holiday cards. So, what if I’m not a “professional” – that’s what makes me stand out. I bet there are plenty of people here who’d much rather come to my low-key, fun-and-done, pop-up session with an “amateur photographer who’s a wiz with her iPhone camera” than an elaborate 1-hour photo shoot. I’d make it all about them. Preview before you buy. 50 bucks a photo (or two or three or 5?) Digital only. Easy peasy. How about local popup photography sessions, just when the light is perfect? A 2-hour window at sunset in a beautiful location, to be disclosed (they need to join my mailing list, or follow my Instagram feed to find out). 10 people @ $50 a pop, 5-10 minutes per shoot. First come, first served. Special rates for pre-payers. Tell a few business owners about it and word will get around. Families, even more so.

    And there you have it: the start of a business idea from the inside out.

    See how I just let it flow there? Let it be messy and organic. Let your imagination run wild.

    Mini Last Step

    One more thing:

    Does this business idea meet your Preferences criteria? If not, don’t fret!

    Now is a great opportunity for making new and interesting connections between your values and your business idea. What creative solutions come up when you do this?

    You know what’s really cool? These solutions or new angles on a business are also what make it unique. I included this in my photography brainstorm already – maybe she doesn’t want to deal with calls and scheduling and rescheduling photo shoots, so she makes it a pop-up – first come, first served. All she has to do is show up; she’s in the driver’s seat.

    Wrapping Up

    I hope you find this exercise useful.

    Like all worthwhile endeavors, starting a business or side hustle deserves input from your truest and most honest self. I believe the best way to tap into “who you are and what you want” is to revisit all those experiences, get it all down on paper, and see what really lights your fire.

    Let’s Have a Conversation:

    What’s your passion, expertise or talent that could turn into a profitable and joyful enterprise?  Try the exercise and share your insights: What surprised you? What inspired you to take action? A toast to your success!

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    Karen Jennings

    Teaching is my passion but after being completely stressed working in the current market, I retired but not to sit still! My church activities, facilitating adult groups, I get to use my skills/experience/ knowledge of theology& Scriptures. Singing in the choir, one of my many hobbies. But now, I may be branching out as a health insurance agent and I’m excited, yet… I am moving forward!

    Kim Neumann

    So great, Karen. Trying something so different can be very stimulating, too. Wishing you success!

    Peggy Carlaw

    Thanks for this, Kim. You’ve got some really great advice here.

    I just started my fourth business at 75…actually fifth if you count my short 1.5 years as a TCM herbalist (had to go back during the 2021 recession to save a company I owned).

    Once I sold that business and retired, I found that I missed having a reason to keep my fingers in technology so instead of continuing as a retired person, I decided to reWIRE and started a new business which I should have ready to launch by the end of the year. The trick for me is to keep it as a side hustle rather than a full-time job. I’m having so much fun!

    Kim Neumann

    So inspiring! Please share once it’s launched!

    Peggy Carlaw

    Hi Kim, Here it is… I’m providing travel tips for people traveling in the second half of life. It’s had a good response so far. Let me know what you think.

    Kim Neumann

    YESSS!! You did it! Love it — clean, beautiful design, smart advice, professional & and a joy to read… your experience shows!

    Marion Edwards

    Thank you, I’m an entrepreneur, reluctant retiree, born, mainly out of the necessity to care for myself as a 70 year, divorcee, choosing to remain single and loving it. It’s been a rollercoaster ride since turning 60, and finding gems, such as your article help guide me along the way. I thoroughly enjoyed reading it and look forward to putting this in to practice, enjoying the process on the way.

    Kim Neumann

    Hi Marion, so glad you found it helpful. And yes – enjoying the process is a great reminder to “slow down & appreciate the little tiny successes.”

    Marion Edwards

    thank you I enjoyed reading your article. Easy to read flows so well and makes a lot of sense in terms of finding myself to create an enjoyable business and lifestyle. Looking forward to putting this into practice and having fun with it:-)


    Thank you for this. I’m an elderly entrepreneur, not out of boredom, but necessity– grey divorce. It is different when one can literally see the limitations on remaining time, energy, etc. Choosing based on passion and talents takes on more importance after decades of doing what was necessary and prescribed. Your article is a worthy exercise to do and learn from and then take into action.

    Kim Neumann

    So glad this was helpful to you, LuAnn. I think especially in circumstances like yours, this exercise can be very grounding and life-affirming… which is also the ideal environment for great ideas to rise to the surface!

    The Author

    Kim Neumann is a one-woman marketing agency based in Marin County, California. With over 20 years of experience and a Master's in Traditional Chinese Medicine, Kim weaves wisdom into actionable advice for DIY business owners at When not strategizing, she enjoys time with her family and spicy Chihuahua, Fonzie.

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