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

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.
Hi Elphas – as a reminder – this is part of our new public posts series sharing conversations with women across tech on the topic of #careergrowth. Please share your perspectives and thoughts in the comments below.Lara, thanks for speaking to us so candidly about your reflections transitioning from full time employee to full time entrepreneur.
I can relate to every word.
Congratulations and welcome to the club ;)One thing I do each year is invest in things I wanted to learn to further my business e.g sales training and I set aside a budget for them. Things that I don't really care for and aren't revenue generating, like bookkeeping, I end up paying for to save myself time.I also spend a lot of time automating stuff, and in recent years have an indispensable VA.Curious to hear and learn about your journey!
I feel every paragraph so hard. Having always been "salaried," stepping out on my own was a serious leap out of my comfort zone. But consulting has been great for developing confidence and I wish more women / URMs could do it! Thanks for sharing your thoughts @larahogan!
The loneliness is definitely something I can relate to, and the importance of building up a team of your own.
What's interesting is the loneliness you describe. I feel this working as a employee. My startup background has well, tainted me somewhat, when working for larger more "traditional" business. I'm just not a good fit. It's not that I don't have good skills. In fact, I find that working for startups I have far more exposure to skills/issues (business, business process redesign as well as tech specific skills) that most of my managers in the larger companies simply do not have. And the "startup mentality", speaking up when you can foresee an issue that could impact project success and providing a plan of action or even, in some cases, stepping up in general, isn't necessarily seen as a positive at more established companies. I do not know what's happening to the world of work, but it just seems like no one really believes in what they're doing, like what they do or cares about much. Is it just me?So i'm looking into doing my own thing more. These days, my work satisfaction is more around surrounding myself with entrepreneurs, who are excited about what they are doing. That excitement and belief is a welcome change to my day-to-day work life. So much so that I do business mentorship and advisory work for social enterprises for free (I just want to be around people who are excited about what their doing and help them be successful). And, it's even turned into working with folks on LinkedIn seeking career advice..My challenge is in finding my "tribe", a group of people I can surround myself with that is of similar mindset. I have that somewhat (thru my social enterprise founders), but want a larger group. Elpha has helped in this regard (at this point i'll take virtual support too), but i'd also like something local. What I recently discovered and would suggest to all feeling the loneliness is to check out groups like Leadercast. I recently found it, and there are groups everywhere that meet up (for the conference and otherwise) and well, encourage each other.I'd also LOVE it, if elpha started conferences/local meetups so that we can support each other both virtually and in person. And, as I'm into podcasts (as I travel frequently), i'd LOVE an elpha podcast about being a female founder. I'm just putting it out there!