5 Essential Lessons from 15 Years of Entrepreneurship

Lessons for life and business

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15 years ago, when I was eight months pregnant, I lost my full-time event planning job in a massive company layoff. I did the only reasonable thing I could think of with my newly available time, and started organizing the homes of perfect strangers. I had no degree, training, certification, funding, or mentorship. I just knew that I really enjoyed helping people clear clutter from their homes and lives, and I had no other good ideas. Luckily it really worked out, and along the way I have learned so many valuable lessons about life and business.

I thought it would be fun, and potentially helpful, to share my most essential takeaways and lessons from the past 15 years of running my own business. I hope these lessons will prove useful whether you are an entrepreneur, considering a side hustle, or just business curious.

Lesson One: Focus on Service Over Ego

Promoting your product, service, or new venture can feel awkward and vulnerable, and it can be so easy to get into your head. I’ve found that when imposter syndrome sneaks in, the best way to get out of my own way is to shift my focus from am I good enough to how can I help? As I matured as a business owner I realized that for me, a more inspiring goal than being the best or most talented or most impressive was to help as many people as I possibly could. Scaling while keeping service first and ego second will result in growth that feeds your spirit and bottom line.

Lesson Two: Commit to Consistency

People notice and appreciate when you are consistent (in life and business) because it builds trust. This is why my rates and hours and policies are consistent no matter who I am working with, and why I post a newsletter every single Tuesday at 5am PST.

Lesson Three: Brief is always Best

People are drawn toward simplicity and clarity, and repelled by noise and confusion. Our human brains are designed to filter out anything unnecessary or confusing, so when writing marketing copy, a social media post, or designing a website - brief is always best. The about section of my website used to have long paragraphs of text, but now it only has a single sentence and some press features. Why? Because nobody really needs to know why I started my company, my dog’s name, or what my favorite flavor of ice cream is (Ben and Jerry’s Half Baked). They just need to know that I can help make their lives better and what they can do to get started.

Lesson Four: Generosity Creates Abundance

Huge lesson: offer value before anyone offers you money. This doesn’t mean you have to give away your product or service for free, but it could mean sharing tips or recommendations, or giving a sample size of what you offer with no expectation of payment or reciprocity. I regularly donate mini versions of my 1:1 packages to schools and nonprofits, host free community workshops, and share everything I think might be valuable right here in this newsletter. The unexpected byproduct of being generous with your expertise, is that it almost always results in highly valuable referrals and connections. The old maxim really is true: the more you give, the more you get.

Lesson Five: Invest in Your Business

When I started my business I was so hesitant to spend any money because - I had no money. I cobbled together a basic website and did all of my own mediocre brand photography. While I made it work, my business and brand really started exploding when I invested in the following:

• Brand photography

• Business coaching

• A custom website

• Educational workshops, programs, and retreats

For the first few years (which were on the lean side) I arranged mutually beneficial trades with other entrepreneurs who were growing their businesses. Once I was a little more successful, I invested in professional photography, a custom website, and regular business coaching and support. Without exception, every one of these services increased my confidence - and my revenue.

Any questions about entrepreneurship? Top takeaways from your own career? Please share in the comments below!

📌 NEW: GET PUBLISHED WORKSHOP

It’s no secret that landing media placements will increase your credibility and visibility, and open new doors and opportunities for you and your business, but the media and publishing world can feel totally impenetrable, and it can seem impossible to get traction without paying for high-priced PR support. After fielding tons of questions over the last couple years about how I got press and landed multiple book deals, I decided to put together a workshop on how to get yourself published with my dear friend, editor, journalist, and author,

Laura Fenton

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Laura and I designed a highly actionable, no-fluff workshop to demystify critical PR skills like connecting with editors, pitching like a pro, and getting your work featured in high profile publications. Join us if you’re interested in learning how to land press and media features for your brand or business - or maybe even a book deal - and become your own PR team! Click the button below to join us!

New Feature:

Chris Guillebeau

just interviewed me for his excellent Substack, A Year of Mental Health. We discussed minimalism, mental health, book recs and more. Read it here.

On my Nightstand: Maria Bamford is a national treasure, and her book Sure I’ll Join Your Cult manages to be both deeply moving and hysterically funny. Linked here.

Summer Swimsuit Recs: Eyeing this chic yet practical once-piece from Andie.

Summer-In-a-Cup-Smoothie: It’s smoothie season at our house, and this one is simple and delicious. Recipe here.