Syllabi, Seeds & Coloring Outside the Lines

Insights from 100 Days. 100 Breakthroughs.

Crisp early mornings. Warm afternoons. Slowly darkening early evening skies. Welcome to September - my favorite month! This longer post is a changeup for me and is inspired by those asking me to share insights from my pro bono coaching challenge: 100 Days. 100 Breakthroughs. This read is for you if you - or someone you know - have left the traditional workforce to launch your initiative - or are seriously considering doing so.

A few weeks ago I announced - 100 Days. 100 Breakthroughs. - my pro bono coaching challenge. I’m offering a complimentary 1-hour coaching session with me to 100 individuals on the brink of something big during the last 100 days of 2023. The idea is to catalyze 100 breakthroughs by year-end. 

If you've shared my LinkedIn post, or offered a comment - thank you for helping me to get this offer in front of the right person. There are still some slots left, so thank you for continuing to spread the word.

Several people have asked me to write about why I'm doing this challenge and to share what's coming up in those coaching conversations and any insights.

So, in this post, I’m sharing three active insights relevant to people who have left their ‘job’ to start their own business selling services or products, and those who are preparing to do so.

Before I go there - let's recap the state of the workforce:

• 60% of today's workforce is quietly quitting, and 

• 51% are actively looking for a new opportunity. (Gallup, 2023).

• Women are leaving their jobs at the highest rate ever, and a higher rate than men. (McKinsey, 2022)

• "I want to be my own boss" is the main reason for leaving traditional work. 60% of teenagers want to start their own business…

• And "workers don't feel like 9-5 is a safe bet anymore." (Harvard Business Review, 2022)

People - especially women - are leaning into career mobility, and many are keen on working for themselves. 

Step Out, Step In

In my career, I've worked across sectors and international borders and stepped out of "traditional work" to step into my creations, including a start-up and a solo coaching and consultancy practice. I've also led change initiatives, collaborated with exceptional leaders during massive periods of transformation, and conducted extensive primary research on reinvention. I'm well acquainted with change.

For the right person, the initial stages of reinvention are exciting - especially the idea stage. But it's normal for that excitement to give way to a feeling of being unmoored.  

As the novelty of the idea of change wears off and the process of transition begins, you're likely to confront situations that challenge fundamental aspects of your identity, values, and ways of being and working, to name a few.

Suddenly, you realize that what seemed like a slight or natural shift is a significant change; this can happen even if you knew you were making a considerable change from the beginning.

The internal dialogue begins; you question, judge, and fear sets in.

• How do I know if I am on the right path?

• Who am I to think I can make a living without a 'job'?

• How do I explain my choices to my partner and friends?

• How do I structure my life? My time? Or, more importantly, how do I know what to do each day?

• What if I can't do this?

• Am I building a business if it is just me?

Through my coaching practice and extensive interviewing of people who have reinvented themselves personally and professionally, I see a pattern: 

Before people are ready to market or sell whatever service or product that will drive their business, they must first step into themselves to

• reimagine their personal and professional self and life, and

• learn how to manage and care for themselves in this new paradigm. 

There's a process required to create this new extension of themselves - their new working identity - and the business idea/entity itself before finally taking it out into the world.

Along the way, they need to support themselves as they quickly build new skills and areas of knowledge.

Even if you initially have clients coming towards you due to leveraging your network and expertise before stepping away from your traditional job, these steps will need to happen eventually. 

As individuals settle into this new space, they soon realize that what got them 'here' won't get them 'there' and that they might be the worst boss they ever had.

And, perhaps most challenging, they usually go it alone.

So my 100 Days | 100 Breakthroughs challenge is about offering 100 people on the brink of something great an hour of space to talk, to question, to challenge, to wonder, and to leave with whatever they came for: affirmation, renewed energy, better prioritization, new perspectives–a way forward. No commitment. No strings.

Here are three active insights from those sessions: syllabi, plant seeds, and color outside the lines.

Syllabi

As of September 23rd, there are 100 days left in the year. Taking a cue from the academic calendar and a page from fellow writer Lyn Slater, one of my suggestions to new solopreneurs and others on the brink of something big is to create a syllabus for yourself.

• Set learning objectives: What will you learn over the next 100 days?

• Set weekly assignments: What experiences can best support that learning?

• Add resources to those assignments: What books, podcasts, or articles might support you in excelling in those assignments? Who might you need to meet? Or who would you like to talk to?

• Incorporate self-care into this plan: How do you want to be over these next 100 days? What existing practices will support you in showing up in that way? What new approaches might you need or want to try?

By carving out a structure for your learning, you will create a dedicated space to work on yourself and your business, rather than focusing only on client work, for example, or feeling pulled in too many directions to support yourself.

Plant Seeds

This week, a client asked me, 'How will I know that I am on the right path?' and shared how scary it feels, 'If I fail or I succeed, it's all on me.' Another, in the US, worried about sustaining access to affordable medical insurance, healthcare, and medications.

Although many people feel very excited about no longer having a "job," the reality is that when you stop working for a single employer and begin to work for yourself, the fear factor is often huge.

Our societal emphasis on getting and keeping a job means we are trained to seek external validation of our professional worth. We don't always view our skills or expertise as 'valid' until we are hired, promoted, and paid accordingly. So, we invest inordinate amounts of time in our on-the-job performance and the organizations in which we work.

As employees, we inadvertently place our professional fates in our employers' or bosses' hands. 

Often, we forget why we were motivated to do that work in the first place. And we yet know that investing in ourselves is the ultimate investment we can make in our careers.

So, taking a page from artists and entrepreneurs worldwide, I advise that new solopreneurs take a long view of themselves and their business ideas. 

• Look at this new phase as a time to plant seeds - in yourself, that personal mission you've got, the business idea or product, or the impact you want to achieve. Seeds that, as you nurture them - and yourself - will grow. Don't expect they will grow to their fullest potential overnight - too many variables are at play to guarantee such "instant" or near-term growth. 

• Instead, like a gardener starting a garden from scratch, be in it for the long haul. Be there when the seedlings break through the soil, when they need watering, when it's time to pick the fruit (or get rid of the weeds), and when the plants grow so large that your garden surpasses your wildest dreams.

Color Outside the Lines

Despite the data indicating that many people are ready to step away from traditional jobs, the reality is that the traditional work paradigm brings most people a sense of security - and it goes beyond the paycheck.

• Job descriptions give us direction and clarity about what we should do at work. They tell us where our job - and someone else's job - begins and ends. They can be a powerful orientating force. Ditto for solid company mission, culture, leadership, and strategy.

• Places of work give us an instant community. People with whom we can collaborate, communicate, celebrate, and commiserate - and connect with outside of work. 

• Jobs give us a sense of our worth, from the compensation and praise we might receive to the simple rhythm accompanying a good day's work.

• Progression at work reinforces the above and gives us a sense of mobility, a reward for experience and expertise.

In exchange for that sense of security - and I say sense because, in reality, there is no security at all - we color inside the lines.

• We follow company policies. 

• Willingly or unwillingly, we adopt and follow company norms.

• We often conform our ways of being or working to adhere to imposed views - of our gender, race, age, experience, and temperament, to name a few.

• And all of the above are influenced by the ups and downs of our company's or team's success.

For many, breaking out of a "job" is the ultimate answer - we can walk away from all that crap. Screw conformity! But, in doing so, we will also walk away from the sense of security offered in the traditional paradigm.

To succeed as a solopreneur or entrepreneur, you must color outside the lines - in all areas. What does that mean?

In short, it means: permit yourself to make things up as you go along - and TAKE ACTION! (But, remember, whatever idea you have, you'll also be the one to implement it…so screen those ideas well.)

• Do you notice someone on LinkedIn who would make a great partner? Reach out and connect; perhaps a collaboration will spark.

• Do you feel lonely - because you are working alone all day? Don’t go it alone. Find your people - those who will champion and support you as you take these crazy new steps. Hint: They're not necessarily the same people who have always supported you, so be prepared to work to find them. Connect. Connect. Connect. Make real connections.

• You have a crazy idea about how to take your service out to the market. Don't overthink it - take it out in its most minor form - to potential customers and get feedback. Keep that creativity moving, and don't let it sit long before you expose ideas to the world and iterate - that's how you will learn.

• Do you have a minimum income requirement? Get creative with how you package your services or products. Try new things - even if you think they're unconventional. Then, take the advice above - share and get feedback. Iterate.

• You want to start writing - or talking - about what you're doing, but you're not sure there's an audience? Start now. Hit publish on that post or video. Get smart about your channel - look for your peeps - they are also looking for you.

• You're feeling burnt out and only two months in; pause. Examine your self-care routine. How do you want to be? What will it take for you to show up that way? I'm meeting more and more solo & entrepreneurs like me who have strict rules about caffeine and alcohol intake, late nights out, and are religious about their self-care and daily practices. Figure out what works for you. Hint: It's likely different than what worked when you had a job.

• You feel financially vulnerable. Assess your situation honestly, especially if this is a new feeling. If paying basic expenses is a struggle, this is probably not the right time to step into your gig. Get a job - even a part-time job - as you build your side hustle, because starting a business from a place of neediness is not helpful to you and not attractive to potential clients. BUT - If you assess your financials and realize that you don't need money, you want money, that’s different. If you’re serious about your new work life, stop doomscrolling and applying for jobs, and, instead, plant seeds in yourself and your business now.

• You aren't feeling confident in how much you know or whether you can do it? Teach someone - another aspiring solopreneur, perhaps. You'll pay it forward and walk away with a better understanding of what you know.

Stepping out of the traditional workforce is the ultimate act of freedom - it's also a crazier step than you may first recognize.

Stepping into your professional creations takes more courage and discipline than you ever knew you had. You will experience different highs and lows than you expect.

And, for the right person, stepping in offers an incredible learning journey and evolution of self - you may discover your most honest life.

What have you discovered as you have stepped out or stepped in? I’d love for you to share in the comments.

Thanks for being here-

PS. I'll share more insights each week, including insights for those who are not ‘stepping out,’ so please subscribe to be the first to read. And, as always, if this post resonates with you, please comment and share it with others.