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Redefining the 9-5 with Upside Member Stephanie Blair

Updated: Jul 13


Upside member Stephanie Blair is an executive coach, consultant and founder of the strategic advisory firm Know & Flourish. She's sharing with us her story from full-time corporate executive on the brink of burnout, to thriving consultant and business owner.


What did you do in your past life before going out on your own?

I started my career in advertising sales for a major NY publisher at the dawn of digital media. This is where I learned that a NO means not right now, that process is KEY to success and that you never know where a new connection can lead you.


Throughout my corporate life, I worked shoulder to shoulder with hundreds of leaders across Fortune 500, SaaS B2B, agencies, consultancies and startups as they underwent digital transformation and growth efforts and saw firsthand the elements that led to success (which usually involved a focus on both tech and people, not either-or).


Having long mentored and developed rising talent, and as someone passionate about contributing to growth strategies that make individuals and modern companies more effective, I decided to launch my own executive coaching and consulting practice, Know & Flourish, committed to “Unlocking high achiever’s potential, providing them with the insight to know and the strategic plan to flourish."


What's your current elevator pitch?

I am an executive coach and consultant focused on grooming and growing innovative talent within sales-centric and growth-focused teams through my strategic advisory firm, Know & Flourish.


I help leaders and their teams more effectively communicate to drive business results and am an expert in digital transformation and in fueling modern organizations for sustainable success.


I also directly partner with leaders to serve as their coach or mentor during times of career transition or rapid change. I'm told by leaders that "having you in my corner is an unequivocal advantage."


How long have you been out of the traditional 9-5?

Over a year now! I left in February 2019.


What made you decide to go out on your own?

I always thought about launching my own business and had been doing coaching for peers and friends and friends of friends on the side for some time. This corresponded with my leadership role at the company changing due to new needs post-merger.


I had a lot of direct reports, and the role was evolving to something that was further and further away from what aligned with my passions - was more operational and less strategic and client-facing.


Despite everyone's best efforts to realign my passions with the business needs, the reality was, it was not possible. Pair this with increased stress due to business and industry pressures (which landed me in the ER), and you have a perfect storm.


It took me landing in the ER to realize that nothing was going to change unless I made the change. I struck out on my own in 2019 and have not looked back!


What do you love most about being out on your own?

I now get to do all of the things I love to do, and can see my impact on high achieving individuals and companies every day.


I'm so proud to have grown and scaled something so quickly and am honored to be able to deliver results to individuals and firms that I'm deeply passionate about helping through periods of transition or accelerated growth.


And it's great to have ownership over my schedule and to be able to arrange my days and weeks in a way that suits my personal and family needs. I'm also commuting a lot less, allowing me more time to get things done!


Who helped you along the way and how did they help?

There are too many people to name!


While I had several mentors and close friends encourage the shift, my biggest champion has and will always be my husband. He has so much support for me and my abilities - he knew if this is what I wanted to do, I would not just do it but excel quickly and make a real impact doing it.


I also had a fantastic high-performance coach who provided me with an operating system of excellence that I applied to my transition and launch process.


And once I launched, I found peers in the Upside who have been incredibly supportive. I'm eternally grateful to everyone who believed in me and who continues to support me on this journey - it takes a village!


How has being an Upside member helped you?

The Upside has helped in a number of ways, first of which is community. Building your own firm can be isolating, so having a community of like-minded, power-house professionals who are also scaling and growing their firms has been essential for me.


It helps from a motivation standpoint but it has also been a place to turn to get assorted points of view on something or when I have technical questions around things like contracts or preferred vendors.


And lastly, I have been able to scale more quickly than I thought as a result of being a member - for example, I found an intern through them and have enjoyed a few speaking opportunities as a result of being in the Upside as well.


What was your biggest stumble and what did you learn from it?

My biggest stumble came early on, when I was trying to be all things to all people. There are not enough hours in the day, yet it's easy to get caught in a cycle of busyness without impact. The Upside has helped me hone my own message and approach to avoid this moving forward.


How did you land your first client?

Many of my first clients were former clients or peers of mine who saw what I was up to on LinkedIn (through my thought leadership and updates on the platform) and thought "I should hire you!" I've since been fortunate enough to have clients re-up and recommend me to others, building out a healthy, consistent pipeline.


I also landed some business early on from the LinkedIn ProFinder service where you get to reply to RFPs and where they try to match client needs with network experts.


What steps do you think professionals should take when first starting a solopreneurship of their own?

  • The first thing they should do is get clear on the value proposition they plan to offer and then find ways to validate that through their own thought leadership on social channels.

  • They need a simple website, in my opinion, to show that they mean business!

  • They should be very mindful of the rate they initially go to market with and know their worth, as where you start is often where you land. The #1 mistake I see people make when starting a solopreneurship is undervaluing themselves and their expertise.

What advice would you give someone who's interested in going out on their own?

I suggest people do an exercise where they think about their ideal state. Then look at their current state and observe how far off they are from their ideal. Then, set out on their own in a way that fuels that vision of their ideal state!


I also recommend bringing authenticity and truth to each interaction.


And lastly, find some accountability partners and people you can turn to when you're not sure whether you should zig or zag or when you hit a rough patch. A coach can be incredibly effective during this time as can joining peer groups like The Upside.


What hack have you learned or created as a solopreneur that you wish the world knew?

One of my favorite things to use with new coaching client is a tool called the StandOut Assessment by Marcus Buckingham which helps people understand their default settings as it pertains to work-related situations.


This has personally helped me and dozens of my executive clients who are determining how and where to make a greater impact.


What do you know now that you wish you knew when first taking that leap into solopreneurship?

It's harder than it looks! While a healthy dose of "I can do anything" is important, it's also important to stay humble, identify your weak spots early so you can find ways to fill them, and always remember that solopreneurship is truly a roller coaster of emotions.


That said, never lose sight of the value you know you can bring to others and get out there and do it. And when you fail or when things don't go 100% to plan, reassess, learn quickly and then get back to it.


Stephanie Blair is an executive coach and consultant focused on grooming and growing innovative talent within sales-centric and growth-focused teams through her strategic advisory firm, Know & Flourish. She helps leaders and their teams more effectively communicate to drive business results and is an expert in digital transformation and in fueling modern organizations for sustainable success. She also directly partners with leaders to serve as their coach or mentor during times of career transition or rapid change.


Want to join The Upside alongside Stephanie and other ambitious consultants who are passionate about flexible, high-impact work? Learn more about membership here.


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