Jen Wilson is a Business Success Coach from Honolulu, Hawaii, who helps women transition from working in their W2 job to being the CEO of their own business.
As a side hustler for 20 years with a Corporate 9-5, she has her feet in both worlds and understands that the success you’ve earned in the Corporate world doesn’t guarantee you’ll make it as an entrepreneur.
You may have just launched your business, or recently started out as an independent rep or agent, and are wondering “How will I get my first or next sale?”
Jen helps female entrepreneurs get out of the weeds to clarify “what’s now” and “what’s next” and take action on only the high-impact activities that move the needle. You’ll get that first or next sale, make it repeatable, and design systems to grow your business as the CEO (and not the W2 employee).
We chatted with Jen to learn more about her business plans as a female entrepreneur.
Name: Jen Wilson
Business: Jen Wilson Business Success Coaching
Education: B.A., Political Science
Location: Honolulu, Hawaii
Describe your most recent business success and tell us about your next big goal.
I’ve recently partnered with a local company to provide a training program to their new agents, who are pursuing a home-based opportunity. Many of these team members come from a Corporate 9-5, and I’ll be helping them bridge the gap between what they learned at Corporate to what they need to succeed as the CEO of their own business.
My next big goal is to meet and get to know more business owners, directors, and team leaders who recruit and build teams, to brainstorm how I might help their new recruits succeed.
How would you define success?
I believe that success is living your life on purpose and with purpose, not allowing anyone else to define you, and writing your own life story. Success means being able to provide and experience the things that are important to you and your family.
What types of customers do you serve and who are you looking to connect with?
I serve female entrepreneurs, who have recently started their own business, either as a side hustle or full-time, most of whom have come from a Corporate 9-5 background. I also serve companies, team leaders and directors who build and develop teams of entrepreneurs pursuing a home-based opportunity.
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If you were not doing this job, what is your plan B? Are you still chasing your dream job?
My plan B is to stay at my 9-5 until my group coaching business is established, sustainable, and I have a trusted team in place.
Yes, I’m still chipping away at my dream business, little by little. Having a day job means that things move slower, but for me, leaving a well paying 9-5 wasn’t an option. Building a business on top of a 9-5 and tending to your family and other responsibilities CAN be done!
Do you think it’s important to love what you do, or make good money?
I think both are important. They’re both elements in the Japanese concept of Ikigai, which I believe is the recipe for being happy and content in what you do. Loosely defined, ikigai is at the intersection of what you love, what you’re good at, what the world needs, and what you can get paid for. Find your ikigai and find happiness in what you do!
Is owning your own business as glamorous as it sounds?
No. Most of the time spent on my business takes place at home, on my laptop. Entrepreneurship can be lonely. If I don’t make an effort to proactively reach out, I can go all day without talking to a single human being.
I wouldn’t be where I am today if I hadn’t made an effort to surround myself with other entrepreneurs. It wasn’t (and isn’t) easy, because it means taking the reins and seeking out new friendships and relationships. As an introvert, that’s hard!
In addition, it was a difficult transition having to sell me and my expertise. There were two choices: make sales or have no business, which were totally foreign concepts to me at my 9-5.
When you trade in your 40-hour a week day job to become your own boss, you’ll work harder and longer than you ever did at your 9-5.
Loneliness, sales, making new friends as an adult, working harder than ever–it’s a far cry from being “glamorous”.
At the end of the day, though, being the Captain of your own ship is well worth it. It allows you to create a legacy and be an example to your family of what it looks like to pursue a life by design.
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What inspired you to start your own business? What made you decide to take the leap?
I think there was always something tugging at me over the many years at my 9-5, but finally, the voice inside my head got louder until I couldn’t ignore it. That was 20 years ago.
I dove in, thinking that it was just about creating an additional stream of income. I sold on eBay, Etsy, Amazon, started making my own baby accessories and gemstone jewelry, sold them to local boutiques, and then started blogging and affiliate marketing.
Every step of the way, I was able to make money, but I kept pivoting because things just weren’t right. Things weren’t right because I wasn’t in alignment.
It took a while for me to know what it was, but once I was able to put words around it (my purpose is to help people choose to live a life on purpose and with purpose), I realized that when my daily actions don’t align with my higher purpose, there is a disconnect and things don’t feel “right”.
I encourage everyone to do the deep work to uncover your life purpose, because when your purpose aligns with what you do every day, you’ll have the clarity that you’ve been seeking.
What was your first job after college?
My first job after college was in insurance claims. I met a lot of good, hard-working, super bright people and learned a ton of valuable skills in customer service, negotiation, influence, and how to communicate effectively in person.
It was a job I intensely disliked but kept out of obligation. Eventually, though, I hit a wall, and I learned it was because I was working a job that was completely out of alignment with my purpose in life. After 20 years, I landed another position (with the same company) as a Coach, where the job and my purpose are aligned, and my life and health have changed dramatically for the better.
What you do every single day has a huge impact on your psyche and your physical health. At first, working an out-of-alignment job might not seem so bad. But the negativity and stress compound (like how a bad habit compounds like compound interest, only negatively) until one day, you crash and are hit with unhealthy physical symptoms.
I’m not saying that you should never work a day in your life at a job you dislike, because I know that’s not realistic for everyone.
BUT, even if you can’t leave your 9-5 because you have bills to pay and responsibilities to take care of, think about starting something small, on the side, that you can grow and that can provide you with options down the road.
What are your tips for setting yourself apart in the workplace?
Be aware and present at work. Take feedback simply as feedback, not as criticism. Listen carefully and be perceptive to what is important to your Manager, the Department, and the Company. Take the initiative and be proactive. Ask questions, take notes, and be interested and eager to learn. Find a mentor.
Understand that you have a personal brand, and ensure you’re developing and cultivating your brand with intention. Always do what you say and be sure what you do, what you say, and the image you put forth are congruent.
If you’re side hustling while working a 9-5, always be sure you’re in compliance and in integrity with your day job.
How do you achieve work/ life balance? How do you unplug?
For women juggling a full-time job, a family, and a side hustle, you’ll often feel out of balance, and that’s ok. The idea is to have “counterbalance.” This means that when life inevitably skews too far in one direction, it’s ok for a season…the key is to ensure that things swing back the other way.
Also, be sure that the “important” things in your life aren’t being neglected. Do this by planning out the upcoming week in advance, and blocking out specific time for the non-negotiable tasks or events (the important, but not necessarily urgent things) on your calendar.
When things feel out of control, anchor to your life purpose. It’ll ground you, remind you why you do what you do, and help you get through the tough times.
As for unplugging—I’m obsessed with pickleball. I started playing four months ago, and I’m able to squeeze in pickleball time when I thought I didn’t have any time to spare! This speaks directly to the above….you can find the time if you’re intentional about it!
What are your plans for expansion?
My plans are to develop group coaching programs to serve and impact more entrepreneurs–to help them successfully make the leap from their Corporate 9-5 to being CEO of their own business and to ultimately live the life they dream of.
What is your favourite product or service for female entrepreneurs?
This isn’t directly related to business, but I cannot live without my ROOMBA, the little circular robot vacuum. It makes me feel productive because I can program it to vacuum a different area of my home every day, and I don’t even have to be at home when this magic cleaning happens!
What books do you find inspiring for building your business as a female entrepreneur?
The most impactful book I’ve read is Mindset by Carol Dweck. I read it years ago, in an attempt to help my son with baseball. What I learned was that the problem was me, and what I perceived to be my son’s problem was actually something I unknowingly taught him (a fixed mindset).
For me, the book was transformational, and continues to help me when I run into an obstacle or when I’ve failed–it helps me reframe the setback or failure as part of the process. It can help any female entrepreneur when they hit a stumbling block (and there will be many), to understand that just because it’s unknown or uncomfortable today, with hard work, perseverance and a growth mindset, they can master whatever they seek to learn.
Interested in the Mindset book by Carol Dweck? Buy your copy online here!
Can you offer any advice for new graduates looking for a job or new entrepreneurs?
The most important thing to focus on at the start of your career or as a new entrepreneur are relationships. Begin meeting new people and develop and nurture relationships over time, because relationships with people will help you more than any technical skill or competency. This is true in business, in your career, and in life.
When my son was recruited to play college baseball, we reflected back on his journey and marveled at the circle of people who had been instrumental to his success: a Coach for our travel team who really cared about him, a hitting coach, a friend’s dad and uncle who both trained him (weights and conditioning), and a speed and agility coach. That was in addition to the numerous coaches he’d had growing up and a very close circle of friends and family who provided support every step of the way.
It takes a village.
As an entrepreneur, you might have the best idea or product or service, but it won’t get off the ground without people. Let’s say you’re a technical genius and discover a revolutionary new way to do something online. How will this be developed and presented to the mass market? How will people find out about it and buy it?
You need people–people to buy into your idea, help spread the word, help you get funding and help find partners and collaborators.
Without people, your business will struggle!
Get to know more people, be genuinely curious about them as human beings, nurture those relationships, and you’ll find opportunities popping up along the way.
Fun fact! Jen Wilson and I met through Marie Forleo’s B-School program in 2023, and I was thrilled to learn more about her business journey. If you’re interested in B-School, read my detailed review online here.
Ways to work together:
- Media Pitching: Work with our team at Pink Pearl PR to pitch your product to major magazines, influencers, and high-profile publications.
- Digital Marketing: Work with our team to develop your search engine optimization (SEO) strategy, or manage your Google ads. Ask us about our unique PR for SEO strategy for female entrepreneurs!
- One-On-One: Work with Talia to create your signature offer and get media ready.
- Coaching and Courses: The Public Relations Academy and Accelerator will help you create your own PR strategy with our guidance.
If you would like to work with me personally to grow your personal brand as a female executive or entrepreneur, you can work with me at Pink Pearl PR. Book a call to see if we’re a good fit. Get on my mailing list for insider perks.
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