There is No Handbook for This
Having no real job and no inbound income is like being stranded on a deserted island. You have to manage your resources well, try not to lose your sanity, while trying to make contact with rescuers (i.e. my network). This is where I find myself these days.
It was a long road to get here, having left a cushy Fortune 500 gig a few years back. I was beckoned by the opportunity to build a company from scratch and to hopefully turn my sweat into a healthy exit. The industry was new to me, the technology was appealing, and the role was full of new challenges. It was a dream scenario. So, after carefully weighing pros and cons with my wife, I decided to take the plunge into the unknown and join this pre-funded company to help it grow. In what seemed like a whirlwind three years and many personal milestones later, I have decided that my best career move is to move on.
There were extreme highs and lows. The highs: Closing a sizable round, bringing in that first big sale. The lows: Not pivoting when we needed to, not making payroll (again). Now in this ether, this aftermath, I underestimated the emotional toll that a startup can have on a family, on relationships and on self-confidence.
Anyone can Google with ease the madcap stories of startups gone wrong. There are all kinds of lists that tell you their version on how to build a successful company. There is no handbook for the behind-the-scenes havoc startup culture has on your emotional well-being. Whether successful or failed, there are periods of time where the payroll will be dodgy. Or times where do-or-die decisions are made. These roller coaster rides are not just impacting the working team, but the significant others that are part of the more critical team back at the home front. And I will tell you: communication and honesty is key.
If you find yourself contemplating joining a startup or if you’re already there, my unsolicited advice is to be honest with yourself about the situation. Consistently review the State of the Startup and understand the risks and rewards. Look around the corner for the wins and the potential pitfalls. Communicate with other stakeholders, which could include friends, family members, and (especially) significant others who also have so much riding on the success of your startup. There should be no surprises on the home front. If rough patches are ahead, the communication ‘seeds’ for those patches should be planted days, weeks or even months in advance. A good home-front manager will see the potential for these things, as I did, and share as quickly as you have the information. In the end, there are still emotional challenges that will require even more communication, some yelling, and maybe some tears.
I am writing the handbook as I go. In the meantime, my confidence doesn’t waver any longer. I know I’m in a better position than I was years ago when I left that cushy Fortune 500 gig. I have earned my ‘street MBA’ through this process, did things that I have never done before, and conquered some old demons along the way. I know I’m better equipped to do great things. I have a brain swelling with ideas. And I know I have the perfect home front team at my side cheering me on.
