Successful Entrepreneurial Ventures & Career Pivots (Webinar Included)

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As a former law firm Equity Shareholder and Office Managing Partner turned Of Counsel Attorney and Small Business Owner, people often approach me with their “professional confession,” “You seem so happy, I wish I had the courage to leave my job, too.” Before hearing these words, “courage” never came to mind as descriptive of my decision to cash in my shares and close my office. At that point, it seemed like the natural next step in my career (a story for another day related to my focus this year, Mental Health & Happiness). This said, making the transition wasn’t haphazard, but an intentional choice that required identifying how I wanted to reshape my career, believing in and acting on my dream, and acquiring the financing to do it, some of the biggest hurdles shared with me regarding why people stay in jobs that make them unhappy. To avoid this fate, read on for ideas for overcoming these hurdles, and others, on your path to pivoting in your career or building the business of your dreams.

Identify Your Passion

Like many of you, for years, I lamented that I had no idea what I would do beyond being a full-time lawyer. The truth is, deep down, I knew I had the skill-set to broaden my career path. The real problem was that I lacked vision about how to serve my clients beyond their legal needs and had not reflected on or planned out my career beyond the practice of law. To do so required analyzing at least two questions:

  1. What brings you joy? It’s often said that you don’t feel like you’re working when you enjoy the work you do. More than likely, your new potential “job” is right under your nose and already a part of your daily life, also meaning that you’re already an expert in your new field. That makes your job identifying your next career step much less daunting. You simply need to think about what you like to do. From mentoring, to running, to mechanics, and everything in between, anything is fair game.
  2. How can that passion be monetized? Determine how what you already enjoy doing recreationally can be transitioned into a product or service that you provide to others as part of a business.

Learn About Your Passion

Growing up, I loved sending hand-written notes. One of my first holiday memories is spending my entire allowance on greeting cards for each member of my family. So, despite that for years I said that I had no idea what I would do in addition to practicing law, had I sooner analyzed the questions above, it might earlier have dawned on me that I would enjoy designing and selling stationery as a part of my career. That said, loving cards and selling them as part of a business are two completely different things. To begin designing and printing stationery, I had to learn about the process, including attending a “paper camp.” Similarly, if you are planning on becoming a lawyer, Elite Lawyer Management may be able to help. The point being, researching the business side of your passion will allow you to best transition what was previously your extracurricular hobby into your new entrepreneurial venture.

Take Action

One of my favorite words is “intentional.” It has meaning. It has grit. It signals that a decision was made and pursued regardless of the outcome. As such, I purposefully started this article by explaining that my career pivot was not “haphazard, but an intentional choice.” If you want to start a new business or career path, you must affirmatively make that decision and act on it. The following may help you do so:

  1. Divide the Goal Over Multiple Tasks: When my husband of now eleven years first proposed, I was a first-year attorney. While the proposal made me swoon, the thought of juggling my newfound career while planning the “big day” was overwhelming. What ultimately made wedding planning whilst lawyering manageable was shifting my mindset from planning “the wedding” to completing a series of tasks. Thinking of dress shopping in January, first dance lessons in February, cake tasting in March, etc. was doable whereas planning “the day of our dreams” seemed completely unachievable. The same logic applies at the beginning of entrepreneurial ventures. “Starting a new business” may sound beyond your capabilities whereas the individual tasks necessary to do so are items that can be accomplished one at a time.
  2. Set Deadlines: Grateful for having learned the value of dissecting projects early in my career, it’s a lesson that’s been applied many times over the years. When something new is encountered that at first seems too challenging, I take a deep breath, divide the challenge into individual parts, and tackle the tasks one by one. The key is to set deadlines by when you will do so. While as the boss you can be flexible if life throws you a curveball, to move from “thinking” about your new business to actually “starting” it, treat the dates selected like appointments that cannot be missed.
  3. Block Time in Your Schedule: As many of us know, it is easy to let things we should do to grow professionally, like following-up with new contacts or celebrating a milestone of a longtime colleague, fall by the wayside when life gets busy. To avoid this problem, a successful local banker calendared two hours every Friday morning to make phone calls and send hand-written notes. She considered the weekly appointment “mandatory,” only cancelling when a true emergency arose. Hearing this story is one of the best pieces of business advice I’ve used to this day. Upon starting an important project, like founding a business, block time to work on it and let almost nothing interrupt your schedule. The difference between an idea and an invention is someone who invests the time necessary to bring the idea to life.
  4. Hold Yourself Accountable: I’ve long been a fan of gym classes. Beyond the camaraderie, it’s much more likely that I’ll actually workout. Whereas when I endeavor to go for a run it gets later and later in the day and eventually never happens, most of the time, if I’ve committed to a class at a certain time, I go. The same logic applies to starting a business. As much as I preach the ideas in this article, in reality, resisting the temptation to move a deadline when life gets busy is tough. What often holds my feet to the fire is committing to someone else. Publishing deadlines, speaking engagements, and other third-party events are what force me to create new content and move the ball forward on behalf of Spread Your Sunshine. If you’re in this boat, too, determine who or what will make you accountable to the schedule you’ve established for your business and enlist such help, including if there is a fee. As I’ve discovered over the years, there is oftentimes value in paying for a deadline.  

Be Willing to Pivot More Than Once

Many entrepreneurs reflect that how they serve their community today is entirely different from where they started. Their community does not judge them because their products and services have changed over time, what made the entrepreneur successful was listening to the needs of their community, continuously evaluating whether their work made them happy, and pivoting as often as necessary to keep those factors aligned. The point is that wherever you start your business is not likely where you will end it. Over time, you will try different things, adapt to new market circumstances, and grow in ways not previously envisioned. The road will be messy and filled with learning opportunities, it is for everyone. So, don’t wait to start your new venture until it is “perfect” or “finished.” It never will be. Just start. That’s what is most important. Your community is here to cheer you on.

Know Your Target Audience

To successfully sell your goods or services, you must identify who wants to buy them. To make such a determination, start by validating your market. Completing such an analysis ensures that your brand, marketing and additional business efforts are all catered to your ideal audience to maximize sales and profits.

Acquire Financing

Whether you’re starting a law office or building a clothing empire, it often takes at least one to three years for a new business to become profitable. To ensure the longevity of your venture, plan for such funding, whether you continue working your full-time job until finances permit you to quit, solicit angel investors, apply for a small business loan, or rely on other resources.

Always Have a Business Plan

A business plan differs from a budget. Budgeting may be difficult before you’re up and running, know what is needed to make your organization work, and can then plan for the future and make adjustments as necessary. To come full circle, what you can, and should, do from the start of your business is focus on how you can uniquely impact the world, set goals for crushing your dreams, and get to work showing everyone around you how brightly you shine. This subject, and the other topics addressed in this article, were at the heart of a recent webinar delivered at the Florida Association for Women Lawyers (“FAWL”) 2020 Annual Summit. Click on the image below for more helpful advice.

And, do YOU have additional tips that will help the SYS community?! We’re sure you do, so please share your advice by emailing me at or messaging Spread Your Sunshine on FacebookInstagramLinkedIn or Twitter. We love hearing from you, as together we are strongest.

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