Making the Most of the Holiday Freeze — How Founders Should Navigate the End of the Year

Dec 3, 2020

Making the Most of the Holiday Freeze – How Founders Should Navigate the End of the Year

Temperatures are starting to drop, year-end projects are wrapping up, and everyone is getting in the holiday spirit. While it can be an enjoyable and festive time of year, it is also one of the most dreaded times for founders. It’s the Holiday Freeze — those awful few weeks between Thanksgiving and the New Year when fundraising efforts slow down, and closing sales gets harder and harder for entrepreneurs. It happens every year, and while 2020 has been a dramatically different year in so many ways, it’s stayed the same in this regard. So how can founders navigate the Holiday Freeze? 

My advice is to take a chill pill. Seriously. 

Every good founder I know is laser-focused on closing. And yes, these guys & gals drink a lot of coffee #glengarryglenross. But year’s end is a tricky time to close new deals. So I often recommend slowing down and spending quality time on existing deals or strategizing on internal activities and save the ‘running through walls’ effort for the new year. You know, chill. 

And because chill for an entrepreneur doesn’t equate to ‘stop,’ here are three ways I suggest entrepreneurs chill out to make the most of the dreaded Holiday Freeze…

1. Set Clear & Realistic Expectations…

Set them for yourself, your team, and your customers/prospects. Be realistic when it comes to your sales and fundraising targets around the end of the year. Many executives and decision-makers will be out of office by December 18th, so don’t expect anything to come across the finish line after then. If you can anticipate the ‘Out of Office’ autoresponders to turn on around that time back into deadlines with your business development team, so you’re not all stressed out the night before Santa comes. This isn’t a normal month, so don’t plan your sales targets like it is. 


2. Reflect & Reset…

While everyone on Earth is ready for 2020 to be over and done with, taking some time to reflect on the highs and lows of the year can help orient you for a successful year ahead. Focus on the things that worked well for your business, document what failed, and assess whether or not changes that were implemented during Covid-19 should become permanent aspects of your business. While it’s hard and uncomfortable for founders to turn off the ‘Closer’ switch, I implore you to take advantage of this downtime and do the messy work that strategy requires. I know that some of you neglect this type of work all year long, stop procrastinating, and get that strategy work done! Reflect on the year behind, reset, and prepare for the year ahead.


3. Actually Chill…

As a founder, your mental and physical health is one of the most, if not THE most, important things contributing to the success of your startup. Without it, the company cannot move forward, your team is held back, and you lose the trust of your investors, stakeholders, and customers. So be sure to take care of yourself when things slow down a bit. Take some time at the end of the year to give yourself the well-deserved break you need. 

And for those of you that just can’t turn off the coffee pot and simply must “A. Always. B. Be. C. Closing”, I found this article from our friends over at Hubspot to be quite helpful. I think they give good advice on how to Close Deals Around the Holidays that any founder can implement today. Check it out if you’re an action-oriented founder who loves a Top 10 list.

With all that, I do hope you all try your hardest to ‘chill’ during the 2020 Holiday Freeze. It’s been one hell of a year and at this point, almost one week into December, I think everyone will be better off reflecting and preparing for 2021 rather than trying to cram new sales and fundraising pushes into the end of 2020. 


Learn How to Make Your Wellbeing a Top-Priority

Your wellbeing as a founder is critical to the overall success of your startup. Read our blog to learn why, and  how you can make your mental and physical health a top-priority.

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