What I’ve learned working for myself vs as an employee - Lara Hogan, ex-Kickstarter and EtsyFeatured

larahogan's profile thumbnaillarahogan·Feb 14, 2019·6 replies
What have you learned working for yourself vs working as an employee?A year ago I started my own business as a coach and consultant, focusing on helping to grow engineering leaders as they support their teams. Before then, I was a VP of Engineering at Kickstarter, and before that, I was an Engineering Director at Etsy. So it was a huge shift when I decided to try my hand at working for myself—no more full-time job, no more full-time team. But I wanted to see what it was like to do a subset of the work I did when I was full-time, and do that subset of work for a spectrum of companies.Doing just the things I love doing (one-on-one coaching and mentoring for managers and leaders, for example) has been an absolute joy. And I am lucky that these are things that people are willing to pay for! I’ve been able to see how the same challenges manifest in different hierarchical structures, different corporate environments, different team sizes, or with different organizational values. It’s been illuminating, and that kind of newness and growth was something I was craving for a while.But I’ve also found how much lonelier it can be when you just need a gut check on something. When I was working full-time, I could always turn to a teammate or a peer leader and ask for their thoughts, or to help me get unstuck, or to help me make sure I was on the right track. Over the last few months, I’ve begun to build more of a team around me, so that I will always have someone awesome who can give me that gut check, or give me some feedback when work goes sideways, or high-five with me when something goes amazingly.Another surprise has been how steep the learning curve is for things like navigating contract negotiations, and what to prepare for taxes or bookkeeping. I consider myself a very detail-oriented person who actually enjoys doing data entry work, so the tasks themselves aren’t tedious for me. But the lack of basic knowledge on where to begin for important paperwork, or what I can push back on in a contract, or what’s “correct” to calculate for the IRS, has been frustrating.The last surprise has been a positive one—that I’ve found it much easier to give constructive criticism and hold my clients accountable as I work with them. I’m not sure exactly why that is; it’s definitely some combination of not having to negotiate a long-lasting direct reporting relationship, and that I’m being explicitly paid to make things better for a team (so that’s gonna involve some hard truths!). But that change has both been refreshing and eye-opening; it’s inspired me to be more clear, timely, and direct with feedback in the rest of my life, too!Lara Hogan is a coach and trainer at Wherewithall. She champions management as a practice within the tech industry, having built and led engineering organizations as an Engineering Director at Etsy and VP of Engineering at Kickstarter. Lara believes it's important to celebrate career achievements with donuts.
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