When to Push Through and When to Pivot

I spent 15 years building a healthcare tech company that we eventually sold to a Fortune 500 company where I became an executive.  We worked hard. We had really long days like any entrepreneurial start up. Hard work, perseverance in the face of mounting uncertainty year over year is critical to the success of a new company. Said simply: the success of a new company is directly correlated to the founder's ability to push through obstacle after obstacle.

Knowing When - Or If - I Should Pivot

Lately, I hear a term come up over and over with my coaching clients. They say,  “heads down, push through.” And I get it, hard work is critical to success. But there's a time to work hard and there is a time to pivot and knowing the difference will ultimately lead to failure or triumph.  

The question is “When do I push harder and when do I pivot?” The success of a company is directly correlated to the founder’s ability to push through obstacle after obstacle, but the wisdom and wherewithal to know when to pull back, reassess, and pivot is just as important.

Unless you are a super-power-project-management-ninja-guru, the tactical side of your business can take you out just as fast as a lack of sales.

This is something that I spent most of my career developing.

What is the balance between setting goals, pushing through, not quitting and pivoting at the right moment to avoid working really, really hard in the wrong direction? One of the biggest mistakes I see in entrepreneurship all the time is this idea of “heads down” at all costs.

How do you know, when your "head's down," if what you’re working on is the thing you need to be working on? Are you ever pulling your head up long enough to ask, “How it’s going?” And, if you do, how do you answer that question?

When You Should Not Be An Entrepreneur

I appreciate hard work.  One of the most important things to me is to focus and finish stuff. In fact, I used to joke that we needed tee-shirts with “focus” on the front and “finish” on the back. I was really serious about finishing. Everyone likes to start, but no one wants to finish. You know that moment when you feel you are 80 percent done, but you are only 50 percent done - and the project drags on, but you have to focus and get it done. If you can’t, you shouldn’t be an entrepreneur.

But you don’t want to finish stuff that is misaligned with your business.

So how do you get that done? How do you ensure that the projects are pointing towards the goal? How do you manage: 15, 20, 40 projects - at times we had 100 competing projects going all at the same time. How do you figure out when to push through when it’s getting difficult -- and when to just call "pivot" and refocus?

Here Is My Best Advice

Set goals on a monthly, quarterly and yearly basis.

What are the goals of the business? Take a day to review what you have completed (hopefully you have tracked them in a program that allows you to print up what you completed). Get really clear on what your global goals are: sales, implementation of a new product, refine systems, hiring, firing, raising money.

Then, make sure you are clear on why that is your goal. If you are not sure why you are doing what you are setting out to do, you will probably give up or change directions without intending to – worse your motivation will be off from day to day.

And by the way, the same process works well for your personal life, too. What do I want to do over the next three months? Do I want to get in shape? Do I want to travel? Do I want to save some money? Do I really want to focus on work? Do I have the time? What are the resources to get that done?

Do You Set Soul-Sucking Goals?

Set Realistic Goals

I know there are some people out there who suggest setting unrealistic goals to motivate you to your next level. I am totally on board with that way of thinking to some degree. But there are stretch goals and there are just depressingly soul sucking goals. Take the time to really assess where you are; where you’d like to be; and if you have the resources to get you there. It sounds amazing to say, we will hit 5 million in one year, but when you come up with 500K in the first year, which would be amazing, you'll feel like a failure. That is just sad. You want to work hard and feel accomplished along the way. 


Ok, here is where it gets dicey. You have set the big goals. You have tapped into that part of you that loves to dream. Now it’s time for the realities of the world to come in and kick your ass. I spent 15 years making dreams become a reality. In truth, by brother would dream up a vision and we’d argue about what was truly possible and what was unrealistic. We’d land on a compromise that was a huge stretch, but had the possibility of coming to fruition.

Then, the real day-to-day work would start up. At first, I have to admit I was a complete disaster. I would try to track hundreds of competing goals and tasks against the shifting realities of day to day life: customer needs, marketplace changes, financial pains, employee challenges. One day I woke up in a state of complete panic. My lists were literally burying me. I was losing my mind.

In a huge self-preservationist move, I created a system that allowed me to meet all my goals (and more) without the stress.

Make Sure Your Dreams Become A Reality -- Without Losing Your Sanity

Here's How:


Sit down with your goals and prioritize them. Seriously, give each goal a number: one, two, three, four. Most people give everything a number one. Or they say, I have 10 #1s, or 1A,  or one A+… You can’t have 10 number one priorities. This is why you are stressed. Rank order your list 1 through whatever number of projects you have. It doesn’t mean you can’t work on 10 things, it just means something has going to be a top priority. Depending on the resources you have, it will clarify what gets the most attention and what gets the leftover attention.

So if you have done this properly you have a list of projects now and the projects are reflective of the goals you have set.

For example, my goal is to start a restaurant in 2017 and get married in the summer. I have 50 projects to get that done. I have to find space, create a brand, get financing, hire a staff, create a menu, and the list goes on. For my wedding, I have to pick a place, buy rings, create a list of guest and again the list goes on.

Your list of projects has to reflect the actual goals. I can’t tell you how often I work with people who have projects that have nothing to do with the goal. Make sure your list is 100% about getting the goals achieved.

Now, you are really going to hate me for saying this, but it will save your life.

Take your list and ask yourself, “What am I doing this week?” I have 5 days (unless you work weekends) to work. What am I going to work on? Hint: it should be easy. Pick the top items on the list. But don’t pick more than you are really going to work on. Again, you can operate from ego and give yourself a list that is not attainable. You can set yourself up for failure or you can set yourself up for success. If you pick a list that will NEVER get done, you will feel terrible. If you pick a list that is achievable, you will wonder if you could have done more. Go with the latter.

What does that look like?

Every week sit down. Ask, “What are you working on?” You should be thinking, “I’m completely clear. I’ve set my goals. I’ve got a list of things. I have prioritized them.” And again, be real. Don’t set goals you can’t accomplish. Don’t set yourself up to fail, set yourself up to win. “This week I am getting back to these 10 people. I am following up on the sales. I am going to hire that employee.”

It’s the exact same thing in your personal life. “I’m going to the gym three times. I’m going to eat more healthy, so I am going to Whole Foods and get healthier food choices -- and make some soup,” right? Really simple, set those goals every week.

Then, take the list of stuff that you aren’t working this week and hide it! Seriously, don’t look at it! If you are not working on it now, forget about it. Worry without action is a waste of energy.


Maybe you set realistic goals, but Wednesday you got a phone call that changed everything. Your child was sick. One of your clients in your business needed something. Don’t be hard on yourself. Something legitimate came up. Another Hint: it’s just life. But, more importantly, when you set your goals you didn’t know an important fact. I set goals on Mondays, but on a Wednesday a huge opportunity came up that I would be a fool to pass on. I can’t get down on myself for changing priorities.

As long as you are intentional, you can never be wrong. This means as long as the new information on Wednesday aligns with your goals, you are doing the right thing in pivoting and re-prioritizing. So many people talk about being heads down, but that is not a good idea.

Working hard is a good thing, but working smart is always better.

Now to keep the momentum going, you’ve got to celebrate the wins, it’s so important. When I learned this lesson, it was the life changing, game changing moment. Every time I would get something done -- like go to the gym -- I’d celebrate. It’s not like I’d pop champagne and celebrate all day long. But, you’ve got to take a moment to just say, “Nice!” or “Done.”

I call it the cookie test.

Do you have a little reward that you love, a little cookie, a cup of hot tea that makes you happy? Whatever makes you feel that warm, happy, calm sense -- you want to muster that up in those moments that you finish something. Do this for yourself. Stop. Pause. It shouldn’t take more than three seconds, and celebrate.

At the end of the week, review the outcome. Did you get your priorities done? Did you set goals that were realistic? Yes? Then, be happy. Really, stop the insanity -- the instant internal conversation about how you have more to do. Of course you do! You will always have more to do. That is why you have next week… you will have more to do until you are six feet under, and even then you will still have something on your list that is not done. That's okay.

Rinse, Wash, Repeat

Look at the outcome, see if you set reasonable goals, then you just rinse, wash, and repeat. Monday, do it again.

So when you realized that you’re pushing really hard and not getting any outcomes you desire or you are getting a ton done, but feel terrible, it’s your process.

Try this process instead.