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3 Years of Solopreneurship: Lessons Learned and Favorite Moments



Three years ago, I made the scary decision to step away from my full-time operator role as VP of People Operations and jump into the unknown world of solopreneurship.


I told myself I’d give it my all for six months to see if I could earn a living as a consultant and could always go back to an operator role if things didn’t work out.


I had clear goals for the life I was trying to design for myself. In this new chapter, I wanted to:

  • Scale the learnings I had gained in my career to help lots & lots of companies

  • Work in areas that I’m most passionate about, which for me was hyper-growth people strategy and remote/distributed work

  • Mentor the next generation of people leaders

  • Select clients that I aligned with philosophically

  • Have greater flexibility with how I spend my time and have more time for myself, my family, and my community

But at the same time, I had so many fears.

  • Do I have the financial stability to step away from the recurring semi-monthly paycheck?

  • Am I ready for the emotional ups and downs, and possible uncertainty that comes with not knowing where my next client will come from?

  • Will it be awkward and uncomfortable to sell myself to potential clients?

  • Will I be lonely?

What a wild ride it’s been! It’s hard to believe that three years have passed. I’m still loving consulting and advising companies and don’t want it to stop anytime soon.


As I reflect on the three-year anniversary of SWC, I thought it’d be helpful to share three learnings and a few of my favorite moments I’ve had along the way.


Learning 1 - Get involved in the community and be a connector


Being a “connector” makes you more valuable to your clients. It can be counter-intuitive for it to be okay to not have all of the answers. The best consultants I know are very niche in their specific offering and know exactly who to call if their clients need support in other areas. To me, it’s such a powerful move to say to a client, “I’m not the best person to solve your problem, but I know who is.” Putting this energy out into the world has brought back countless moments of joy for me as I’ve grown my business.


You have to purposely cultivate this network, though. It won’t come to you. Attend industry events, join online forums, and connect with other consultants. This is a great way to learn from others, share your knowledge, and build relationships. The more you give, the more you’ll get back. Having an abundance mindset is key!


Learning 2 - Support people leaders from behind-the-scenes


People leaders have been through so much these last three years. Being heads-down in an operator role, keeping up with meetings and your day-to-day responsibilities does not leave much time for creative thinking, problem-solving, and personal growth. One counter-intuitive learning for me has been the unexpected joy that comes from partnering with people leaders behind-the-scenes. Helping set them up for success by providing them the space to think long-term and develop in their roles.


There is a stereotype that consultants stop learning the moment they step out of an operator role, but I have found my experience to be the opposite. Given I’m not bogged down by back-to-back meetings, my brain has much more space to stay on top of the latest research and innovation, helping my clients get unstuck and think about solving problems in a new way. There is no greater joy than helping someone else succeed!


Learning 3 - Invest in your mental health


Being a consultant can be lonely when you no longer have a team to brainstorm and collaborate with every day. Your mental health can also be impacted by the added stress of running a small business and generating your own leads. Balance is key and setting boundaries for what you are willing and unwilling to do is essential.


“Do whatever gives you the most energy because energy is that currency that drives everything else.” - Tim Ferriss

One of my greatest learnings along the way has been setting earnings minimums and maximums. When first starting a consulting business, it is a useful exercise to identify the minimum you need to earn to meet your financial needs and live your life. And of course, you can model scenarios above that earnings amount to set a more ambitious goal for yourself.


However, there’s a negative side to earning as well where you hustle to grow your business but at what cost? I have found it useful to set maximums too – what is the max number of income I want to earn in a year to feel that I can slow down on business development, feel successful, and live my life? What is the max number of clients I can take on to provide them excellent service while still having the time I want to devote to my family, mental health, personal interests, and hobbies?


Bonus Learning 4 - Enjoy the journey


Prior to starting my own company, I was a people leader at four high-growth unicorn tech companies. I was used to celebrating company milestones in a big, fun way at company retreats each year. Now that I have my own business, I’ve made a point of celebrating SWC’s anniversary by going on a “company retreat” each year. I fly to an inspiring location for at least a week to relax, celebrate, and reflect on the year ahead. So far, I’ve been to a surf and yoga retreat in Nosara, Costa Rica, and a cooking tour in Oaxaca, Mexico. Later this month I’m heading to Bali, Indonesia for more wellness and adventure, and can’t wait!! Let me know if you have favorite retreat centers around the world that I should consider for future years. Maybe, we could go together!


"The only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle." - Steve Jobs

In closing, stepping away from that steady paycheck and going for it on your own can be terrifying. I’m so glad I did because I’ve had the opportunity to work with amazing clients, work less while earning more, spend more time with my family, and friends, and engage in my community.


My story is not unique. If I can do this, so can you. But don’t be afraid to ask for help.


If you’re considering a similar path of going out on your own, but don’t know where to start, check out my Consultant Getting Started Guide.


If you’re considering a side hustle of advising companies on product and go-to-market strategy, check out my Product Advisor Getting Started Guide.


Want to talk 1:1 about your goal of solopreneurship? Book an “Ask Me Anything” session today!


I’m excited for what’s to come in year four and beyond. Cheers to you and thank you for your support along the way!


Shelby

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