With the holidays coming up, most of the world is looking forward to taking a week or two off from work, spend time relaxing, vacationing and spending time with family. Not entrepreneurs!
While most sane founders do, of course, spend at least a few days soaking in the holiday cheer with their loved ones, we can’t help continuing to work on our business to prepare for an even stronger new year -- especially because we know our competitors are doing the same.
The problem is that it can sometimes be difficult to determine what to work on over the holidays. Late December is traditionally a terrible time to raise money, recruit employees, close deals or even make progress on key product or engineering milestones, since most of our teams, partners and investors are taking their hard-earned vacations. Once we’re caught up on outstanding communications and budgeting stuff, we can often feel frozen and at a loss for what to work on.
I certainly felt this way during my first winter or two running Brainscape. Yet, as I’ve developed my own management processes and communication strategies, I’ve learned to set aside the holidays for five key themes that allow me to successfully regroup for the new year.
1. Strategic planning
By mid-December, you have hopefully drafted and communicated a strategic plan for the coming year already. But the holidays are also a great time for you to refine that plan and prepare for a successful kickoff when your team returns to work. It’s often a good idea to start your new year with an all-hands meeting that launches various task forces and gets everyone re-aligned around your mission and vision.
To maximize the effectiveness of this all-hands meeting in early January, I recommend starting work on a discussion at the beginning of the holidays and keeping the file open to continue tweaking as new ideas keep coming to you during those quiet office days.
2. Meeting planning
As you iterate on your strategic plan during the holidays, you’ll likely have many additional ideas for new task forces and one-on-one conversations that could help your employees get a fresh start on the new year. The holidays are a great time to build all those upcoming meeting agendas. Keep a running list of possible talking points for your upcoming one-on-one meetings with each employee.
3. Thought leadership
If you’re like me, you probably have many ideas for blog posts or speaking gigs that would help you promote your company’s mission or its smart business tactics via a variety of media channels. The problem is that we rarely have time to write these articles!
The quiet holiday season is a great time to catch up on our long backlog of blog-writing and conference presentation proposals. My dirty secret is that I pre-write drafts of many of my articles over the holidays, so that they’re ready to gradually submit over the coming months with minimal last-minute editing.
Most successful entrepreneurs get where we are with the help of dozens of key advisors, investors, partners, users and other founder friends. The holidays are a great time to thank these people for all their great advice and support. Whether you send a giant blast of emails or write classy individual hand-written notes, you’ll find that gratitude will both improve your personal brand and make you a happier person in general.
5. List refreshment
I’ve previously written about the 20 lists that every entrepreneur should maintain. This includes both short- and long-term to-do lists as well as lists of investors, journalists, partners, supporters and acquirers that you want to keep in touch with. Such lists can naturally become stale over time, and the slow holiday season is a great time to review your lists and update your notes and status columns for each entry to reflect your new realities.
Of course, if you have a consumer or ecommerce business whose strongest sales come over the holidays, then you should still use the holidays to focus on selling, and ensure that you are capturing and reporting revenue in the most effective way possible.
But, in the event that you have some down time as the rest of the world regroups, the above suggestions should help position you and your business for the strongest new year possible.
Feel free to add any other holiday entrepreneur suggestions in the comments below.