Leaping with guardrails – managing risks when making big decisions
Our next article is out - a summary of our conversation with Abby Sugar, CEO and Founder of Play Out Apparel! In our conversation with her we learned how she was able to manage and reduce risks associated with founding a company, and in our article we share how her lessons can be applied to leaps more broadly.
We recently caught up with Abby Sugar, Founder and CEO of Play Out Apparel. Founding Play Out was a huge leap for Abby; she didn’t have prior expertise in fashion or apparel but was fueled by a desire to create an inclusive place where she and others could shop. In our conversation, Abby shared a few risks that she weighed in founding and leading her company and how she managed those risks. Her takeaways apply broadly – not just to new or seasoned entrepreneurs but for anyone thinking of taking a big leap and unsure how to manage the risks associated with it.
1. Risk of failure – Manage with self-awareness
2. Risk of a lack of experience – Identify gaps and ways to fill them
3. Risk of focusing on the “wrong thing” – Set your direction, metrics, and reflection points
Risk of failure – Manage with self-awareness
While the risk of failure when taking a leap can encompass several elements, one theme from Abby’s journey was the role self-awareness plays as part of that. For Abby, she was working 3 jobs in a day and then trying to work on her start-up late into the evening. She did this for a while, because at that time, quitting felt too risky. However, Abby reached a point when she realized if she didn’t try and do it full-time, that was something she’d always regret – regardless of whether the company succeeded or failed. She knew her skill sets and knew that even if she hadn’t founded a company before, that she had solved tough problems and had enough idea of where to start. What we can learn from Abby is some of the subcomponents of self-awareness 1) continuing to evaluate our risk appetite – what feels ‘too risky’ now might change over time, 2) understanding our own strengths to create that internal narrative of “I can do this” and 3) visualizing a future in which we do this and it goes well or goes poorly, and checking if we are comfortable with either of those paths. Underlying this self-awareness was also Abby’s clarity about the ‘enablers’ which allowed her to take this leap – such as her personal savings – which mitigated the financial risk for her.
Risk of a lack of experience – Identify gaps and ways fill them
Following on from Abby’s self-awareness about her skill set, she knew that one risk of deciding to pursue this full time was not having some of the business or technical expertise to execute on her vision. In her case, she was able to reduce this risk through an accelerator program she participated in. That accelerator required her to move across the country, which she was in a position to do, and provided coaching, support, training, and a community of founders. Abby did not have a business background but had a supportive environment to learn what she needed through this accelerator program. For other entrepreneurs, this might mean building out a team with complementary skill sets, but for leaps generally, building experience quickly could involve taking classes in a new field, talking to people, or extensively reading/researching the topic. Identifying the components of leaps that stem from lack of experience and then filling them in a way that’s manageable to your own journey can help de-risk that aspect of the decision.
Risk of focusing on the “wrong thing” – Set your direction, metrics, and reflection points
Often, leaps aren’t a clear step from point A to point B and involve many decisions along the way (or once you get to point B). In Abby’s case, founding a company was so much more than the decision to go for it full time – where should she focus her time, what products should she prioritize and sell, and how? As Abby described it, she’s “not a 5-year plan” type of person, but she still set targets, such as funding, that if she didn’t achieve after a set time, that she’d walk away. Though she didn’t have a more traditional strategy, she was guided by the mission of her company, key metrics to focus on, and defined clear points to pull up and evaluate whether to continue to move forward. Setting these ‘stage-gates’ or pull up points saved her from constantly weighing whether we should or shouldn’t be doing something – it puts that decision, reflection, and evaluation off until we reach a point where we have enough ‘data’, experiences, or any other information is needed to make that call more accurately.
While these risks and examples are more entrepreneurial in nature, they can apply broadly to any leap. The nature of leaps is that they are risky - if it doesn’t feel risky, it’s probably a step and not a leap. However, by cultivating self-awareness, filling gaps in experience or expertise, and following a clear direction, that risk can be reduced in hopes of a more ‘successful’ leap, by whatever definition we choose.
