The Art of Risk-Taking: Creative Strategies to Facing the Uncertain

Los Angeles last month saw the largest annual gathering of Jewish community visionaries, activists, and catalyzers of change in North America, led in partnership by UpStart and ROI Community, the Collaboratory.

This year’s topic of the Collaboratory was ‘The Art of Risk Taking’. The ability to navigate risk is one of the most useful skills to have in our professional and personal lives. No journey is risk free and being able to face risk, evaluate it and overcome it often differentiates between success and failure, happiness and unhappiness. According to difficulty is the reward, we read in Pirkei Avot (The Ethics of the Fathers), and risk adds to the difficulty.

Those who succeed take risks. In truth, “I wish I had taken more risks” is one of most common regrets people cite at the end of their lives. Many feel that the possibility of failure made them play too safe. They also felt that taking more risk and disturbing the status quo would have yielded a more fulfilling life.

Risk-taking is an art. And there is a science to this art. We make about 35,000 decisions per day – from the moment we open our eyes and decide (not) to turn off the alarm clock. As children, we only face around 3,000 decisions per day so adulthood is quite an upgrade to this gamble.

Knowing which risks to take and how to take them can be a powerful tool to stack the odds in our favor. Some of the basic pieces of advice to face the risk include to have as much information as possible, assess risk, and learn from failure. In order to hone your risk-taking skills more, here are a few guidelines from design thinking – an approach that uses creative strategies to problem solving.

  1. Challenge the assumptions: Think outside the box and challenge even the long-held beliefs. Sometime we fail because we cannot let go of the past but it is impossible to assess the future if we are only headed backwards. Learn from the past mistakes but move on.
  2. Ask why: Always ask why, even if you think that you know the answer. More often than not, you may learn that you actually don’t know the answer. The answer can also surprise you and expose the uncertain ahead.
  3. Identify inconsistencies: Sometimes what people say and what people do are two different things. Observe behaviors of those around you and be on the lookout for inconsistencies – they can flash out the potential risks.
  4. Be empathetic: Empathy is one of the key principles of design thinking. It forces us to imagine “walking in someone else’s shoes” thus revealing challenges and concerns around us.
  5. Encourage stories: Stories might not predict future risks well but they expose the breadth of the views and opinions in the world. Stories can unearth perspectives and solutions that have not been considered yet.

Life, in all its beauty and struggle, is unpredictable. Every decision we make has a margin of risk and the life we end up living depends on those decisions. While there always is a chance that our desired tomorrow will never come or the actual tomorrow will never come, there are risks in our professional and private lives that are worth taking because they are almost always necessary ingredients in the recipe that is success and happiness.

And the last piece of advice comes from the great French poet Rene Char:

“Trust firmly in your luck, cling to your happiness and dare to take risks. They will see you and learn to accept you.”

Creating a Non-profit Content Calendar – the Easy Way

There are myriad reasons why your non-profit needs to be sharing content regularly on your website and social media. For staying top of mind, reminding people of the work that you do, getting your message out (and furthering your mission), and even basic SEO strategy, content is king.

But between all of the other seemingly more pressing, mission-critical (pun intended) things your team does every day, creating and sharing content seems like a last priority. So while many organizations are aware of the “need” to publish, few do. And even fewer do it with any sort of regularity.

1. Planning Your Non-profit Content Calendar

Creating a calendar is a simple, effective way of scheduling future posts, but, if done right, makes it a lot easier to actually generate those posts. Chances are that you already have a calendar that includes major events like galas, do-good drives, annual events and celebrations, among other things.

That’s actually a great starting point for creating your content calendar, since you know you want to be promoting these events before they happen, and talking about them afterward. Thinking of those events as “content-worthy” ahead of time will likely spark ideas of things you can do and share online well in advance. Put those things on your calendar!

For calendaring and planning, I love the free and powerful Asana, which can integrate with but the best tool is the one you are most comfortable with…even if it’s the whiteboard in your office.

I recommend keeping an ongoing 1-year, 6-month, 3-month, and 1-month calendar. The further away something is, the less detailed the plan has to be. For the sake of sanity, however, anything in the 3-month window should be in prep, anything in the 1-month should be in “production,” one way or another.

Once you’ve got your major dates and content plans, you’ll likely need to add more items. So what do you add? Read on.

2. Create the Right Content for Your Non-profit’s Audience

This seems simple on the surface: Engage with your audience on the subjects that they’re interested in. The more value you provide and the more you show them that you share their interests and concerns, the more personally connected to you and your cause they will be.

The problem is that, most of the time, businesses and organizations focus on just talking about their work; or worse, asking for the sale or donation. Your audience is probably interested in other things, many of which indirectly connect back to the change you want to make in the world.

For example, if you’re a New York City theater company focusing on children’s theater, there are many areas of interest that overlap with yours, which your audience (parents of New York children) might be passionate about, or at least just interested in. New York arts festivals and arts funding news are an easy extension of news you want to share. Then there’s national and local education news, studies about the impact of imagination and storytelling, arts in education, or even that it’s a snow day!

Don’t worry about experimenting and getting it “wrong.” As long as you don’t offend or alienate people, trying different tacks may yield surprising results. With time, the more content you share, the more you’ll see what your fans respond to, with likes, shares, and website traffic. Spending a little time (and possibly sending out a survey) thinking of ideas that your audience will appreciate can go a long way and pay off greatly in the long run.

Sharing content about current events may seem like a full-time job on its own, but with a little planning, it may be easier and less resource-intensive than you might think. Which takes us to the “shortcut” in the next section…

3. Timeliness and Tie-Ins for Your Content Calendar

One of my favorite ways to generate quality, valuable content that speaks to audiences on multiple levels and isn’t all about “me” is by tying it into events happening in the world. As a bonus, people will already be thinking and talking about the subject at that time, so you may enjoy a viral boost. While you can’t plan for the latest news headline, you can plan for national holidays and, more apropos for nonprofits, awareness days, weeks and months. To make it easy to find and add these dates to your calendar, dotOrgStrategy has created a new non-profit awareness calendar feature, including links to websites with more information and hashtags you can use to join the conversation.

There are nationally-recognized philanthropic events like National Volunteer Week, and more specific ones for arts and culture. If you’re an organization dealing with health-related concerns, there is no shortage of awareness dates to tie into. For others, you may have to think a bit more creatively, but that can also be freeing and fun. For example, what’s your organization’s position on television, toilets, fathers, or the U.S. flag?

Whether you want to say something fun or poignant on social media, or to make a larger statement with an article or video, there are sure to be plenty of things to talk about when you keep track of awareness calendar dates.


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