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Big Ideas

Grin and Bear It: How to Tackle Your Tougher Tasks

11 tips for your most difficult and dreaded workday tasks from J.J. Ramberg host of Your Business on MSNBC and author of "It's Your Business."

When your to-do list has a stubborn item that has been there for days, it’s time to call in outside help. As host of Your Business, J.J. Ramberg has interviewed hundred of entrepreneurs and compiled their wisdom in 183 bite-sized tips in her new book It’s Your Business.

Because we’re all about reducing the friction for idea execution here at 99U, we were particularly interested in the tips from entrepreneurs about how they handle the tasks we all tend to put off.We shortlisted some of our “favorite” pain points, and paired them with great insights from IYB:

Disagreements With Your Team

Create a disagreement protocol (Tip #60)Fighting can be good for the creative process, but left unchecked it creates an atmosphere of resentment. To avoid this, create a “disagreement protocol” that spells out what your team should do if they can’t agree on something. This minimizes gossip and keeps everyone on the same page. From Ramberg:

Here’s Michael Bosma’s policy [Founder of the Bosma Group] If someone is on a rant about someone else, they should speak about the problem directly with that person. If someone complains to Michael, the first thing he does is ask if they addressed it directly. This immediately ends the gossip.  New members to Michael’s team tell him it’s the most positive work environment they have encountered

Stuck in a Rut

Swap jobs (Tip #49) – When your team feels stagnant, temporarily switch roles. This can be especially effective at the senior level.

Open up your brainstorming meetings (Tip #25)– Occasionally invite folks from other departments and require that they contribute at your brainstorming meetings. The tech folks may have a new approach to marketing and vice-versa. In case of larger emergencies, invite your entire staff and pitch the problem you are facing.

Get fresh ideas from your team’s brainstorming meeting (Tip #14) – Before the meeting, email your team the brainstorming topic and require that everyone bring ideas, no matter how unfinished. Then, at the meeting, go around the room one-by-one. This gives the more introverted staff members a chance to participate. “As is the nature of brainstorming meetings, these good ideas will then spark the group to generate even better ideas,” writes Ramberg.


Get past the corporate gatekeeper (Tip #86) – Email important contacts before or after hours to avoid being intercepted by assistants. Many executives work late, long after their assistant goes home for the day.

Call all leads within 15 minutes (Tip #90) – In your case it may not be a “lead” or even 15 minutes, but contact people as quickly as possible after they show interest in you or your company. The chance they will change their mind decreases the less time you waste, and you’ll impress with your responsiveness.

Be the first one at every event (Tip #147) – Arriving to a new event alone after everyone has already grouped off can be awkward. It’s much easier to socialize earlier on, as people are more likely to be by themselves. Alternatively, notify the organization that planned the event that you are new and ask to be introduced to a few folks during a tour.

Marketing Yourself

Be ready with photos on your phone (Tip #12) – You never know when you’ll be in a position to explain more about your work. Save photos and presentation files on your phone to help supplement any impromptu elevator pitches.

Create a personal story to connect with customers (Tip #136) – Especially for small businesses, the people you interact with will be curious about your story. As a bonus, by telling your story you can ensure you’ll be memorable.

Have your photo taken (Tip #134) – Spend the money to have a professional headshot taken. You’ll be ready when you speak at conferences or are covered by a media outlet that doesn’t send their own photographer, which is increasingly common.

Other Unpleasant Tasks

Knock off unpleasant tasks first thing in the morning (Tip #42) – For everything else, just make sure you handle it as early in the day as possible. From Ramberg:

I pressed “snooze” about ten times on my Outlook-calendar reminder that I had to “Call landlord to discuss my office lease.” … I found fifty-five reasons why it was a very important to clean my desk or decorate the office… When I finally did call the landlord everything worked out and I wished that I had done it earlier so it had not being weighing on my mind all day.

What About You?

What are your most unpleasant daily tasks? How do you tackle them?

More Posts by J.J. Ramberg

Comments (7)
  • Nit Picker

    The title should be “Grin and Bear It”… Unless we’re talking about taking it all off for productivity!

  • Sean Blanda

    I didn’t think you were correct and then I grabbed the dictionary to double check. Good catch! It’s been fixed.

  • Ton
  • Jacques van Heerden

    I always believe to jump in the deep in first. Getting your hardest tasks done, can be so much more rewarding later on.

    Initially you will feel that you want to complete the easy tasks first, but getting the hard ones done first will free up some time later in the day.

    Try it.

  • Scott Sullivan

    There are some good tips in there. I will be looking forward to checking out the full publication. I have to say, though, that I have a small issue with “#134: [Have/use] professional photos [of yourself]”. I’m aware of the psychology behind this concept cited by proponents and I would even concede that the world does work “that” way; however, that’s a long conversation. In short, I would amend #134 to include having or using a professional logo is equivalent or better to an image of your visage.

    At the end of the day we are talking about branding. It makes sense for a sales person to “brand themselves”, but I argue that you can never go wrong when you build your brand like the big boys do. Google “most recognizable logos” and think about it, then engage me if you want to get into the details. Before I go, I’d like to add my own tip to the pile. It’s a philosophical point about focus, leadership, and productivity. My tip is….

    == The “top three” goals (Tip #1.618) ==

    No matter how long your todo list is or how clearly you can see the path to your ends take it and communicate it in small doses. You can still have a todo list a mile long, but only the “top three” are given focus- everything else is just “next”.

    Write the “top three” down, especially if you are leading a team, and as they are completed cross them off. I mean literally draw a line through them. Make a celebration of the fact. The time-scale varies for expected completion of your “top three”.

    It may be three goals/tasks to accomplish: today, this week, this quarter, et cetera. For my personal action items I use the day time-scale. Leading an executive team/peers the quarter time-scale works well and for leading the bulk of a team/staff/business the week time-scale is often the best.

    There are some finer points that stem from this root ideal, but I’ll leave that discourse for the next soapbox….. end transmission.

  • Jack Peterson

    Great article. I use this planner and put those tough tasks as “Mission Critical”

  • Dawa Sherpa

    Great post. i enjoyed the article and the tips provided. I always like books that have bite sized advices. I’m sure that I’ll enjoy this book. A similar book with advice from great entrepreneurs with bite sized advices is Rework.

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