Step Ten: Stay the Course

Stay the Course is step ten of the ten-step Maturepreneurial series How to Start a Business After 40.

image of sailboat on still waters

Hugo Kerr

Stay the course

Step ten, like step two, is a step I personally find challenging to fulfill. Once I start something new, after a time that might be short or long depending on the circumstances, I will tend to feel “lost at sea.” I manage to take the first steps of the journey and see initial progress. I may also still see great future promise.

And yet.

I begin to experience existential angst.

And self doubt.

I ask myself questions like:

  • Is this all there is?
  • Why do I feel like I’m not getting anywhere?
  • Am I looking too soon or too hard for results?
  • Am I micromanaging myself?

Partly, I would say the latter is true. If not myself, then at least I have a tendency to micromanage the process (which spiritual teachers would argue is the self). In any event, this is a symptom of my orientation towards results and outcomes. If your work, your effort, your focus, or your attention are all about the outcomes they’re expected to provide, then you’ve probably lost touch with any meaning, and therefore joy, the process itself can bring you. I’ve certainly done it enough times to know.

Weather the doldrums

Successfully staying the course – any course – to me, means not losing faith, courage, or heart when I’m “in the doldrums.”

In maritime usage, the doldrums are places in the ocean near the equator where the prevailing winds are calm. In fact, the wind can disappear altogether, leaving sail boats trapped or stranded for days or weeks at a time.

That’s kind of how I feel after the initial rush of starting something new and having to consistently apply myself to it without seeing a lot of change or progress. I feel stagnant. And in that stillness or absence of momentum, I start to question myself and whether I’m doing the right thing; i.e, pursuing the proper course to achieve my goals in the first place.

I also feel a little bit guilty: I’m not fulfilling my potential. And somehow that’s my fault.

The good news is: now I understand this human experience is not uncommon. And entrepreneurs are no less susceptible to the doldrums than anyone else who feels trapped by their choices as the consequences play themselves out, perhaps more slowly than they would wish. Sometimes they play out with drama, excitement, or rewarding milestones. Often they play out with little to show for the time and effort we put into our work.

“Never give up”

At times like these, I find comfort and inspiration in what Chuck Gumbert has to say about this stage of the entrepreneurial journey.

“Sit back, establish a series of goals, and then develop some plans to go accomplish those goals. And then the biggest piece of it is, have the gumption to stay the course. Never give up. Never give up.

Chuck goes on to talk about correcting course. He says, “There’s nothing wrong with changing tactics.” But he also says that you have to keep your eye on the goal and keep working towards it.

“Don’t change the goal. And don’t give up.”

Jason Treu also talks about staying the course. He says that most businesses take four to five years to reach maturity, so committing to the long haul is necessary to reach the end goal.

You have to make big bets and spend time on things, but they aren’t always going to work. And you just have to keep doing them. That’s the hardest part of being an entrepreneur and starting a business and trying to think bigger down the road, is that you just don’t know what’s going to happen. And you have to believe that you will find the right path and things will work themselves out over time.

Jason cautions entrepreneurs against looking around, especially in the online space where so many businesses proliferate today, and feeling daunted by people who claim to have built businesses in a very short time span. Jason believes that, even where these claims are true, eventually those businesses will plateau. They will reach a point where as much time and patience are required of them to stay the course as is required in businesses slower to gain traction.

If you’re thinking about having a business in 24 months that is going to explode and take off, I’m here to tell you that those are a very small minority and if they do, they’ll eventually plateau and they’ll still be stuck. And then they won’t know what to do either. So everyone’s going to reach that point. It’s one of those things that you just have to understand and have in the back of your head. And then I think you can build a sustainable business that’s really successful over a long period of time.

Henry Lopez takes a similar view. He believes that “determined, steady and consistent work” is what moves a business forward and eventually leads to success. You have to understand that failure and setbacks are part of the entrepreneurial journey. He attributes his own success to “some lucky opportunities and breaks and some being at the right place at the right time but a methodical and consistent approach to developing my businesses.”

In his episode, Dave Mancuso says, “It took about two years for me to find the right clients that created the synergy for my business to move forward.” He makes the encouraging observation that once you do find some of the right clients, you tend to start finding more like them.

Dave also talks about not giving up. “Every time I’ve stumbled, I’ve found out that it was actually an opportunity to move forward and not necessarily fall down and stop.”

Like Dave and Henry, Douglas Burdett also found success in the long play.

It was a pretty steady climb. If you look at the analytics for my podcast, The Marketing Book podcast, you will see that there are no big spikes, but it’s just a real steady climb of listeners. So, it’s the same sort of thing where, I would say, that your listeners should probably be expecting the worst and plan for that.

Playing the odds

Dinesh Kandanchatha offers similar and very helpful insights into the entrepreneurial life.

“For every good idea, there’s roughly six bad ideas. The problem is that you don’t get to the good idea unless you run through the bad ones.”

In order to do that, you need to execute on your ideas and give them time to develop. Dinesh says, “The key thing is to start them and ascertain quickly whether or not they’re taking you on your way.”

Dinesh does not shy away from his mistakes or failures. When Elaine asked him what was his least successful idea and how did he change tactics to fix it, he first answered, “Oh dear, that’s a long list! How many hours do you have?” He’s had new product launches that “failed abysmally.” One of his companies was sued and put into bankruptcy for IP infringement. However, like Chuck Gumbert, Dinesh reiterates that you can’t give up.

The reality is, again, that’s how the game is played. So if you’re worried about bad ideas this is the wrong business to be in. Don’t be in entrepreneurship if you’re worried about getting things wrong. You’ve got to get used to failure and get used to getting back up again and dusting yourself off.

Dinesh talks about learning from not only mistakes, but from the very process of executing on your ideas. That is how you discover and test your personal limits, the limits of your market, the limits of your team, the limits of your business. If something doesn’t work the way you expected it to, pivot. It’s a necessary part of business growth and development.

Dinesh speaks directly to staying the course when he offers the following advice:

Be prepared for it to take longer than you think. And what that means is, decide if it’s something you’re willing to spend the next five years doing. Most entrepreneurs think this is going to be a one year journey, or a two year journey, maybe three years at the outside. And you know, our time is valuable as we get older. We personally value it more. So whatever you choose to do with your time, especially as it relates to entrepreneurship, make sure it’s something you’re going to be willing to commit the next five years to. Otherwise, don’t start it. It has to be strong enough that you’re willing to say, ‘I’m going to spend five years trying to make this work.’ I think that’s a great crystallizing idea that will help you decide if that business you want to start, that thing you want to do, is worth that much of the time that you have.

In his personal experience as an entrepreneur and in working and networking with entrepreneurs of all different ages, Dinesh has observed that opportunities in business life cycles seem to arise at five year marks. Dinesh attributes this timing to the human body clock and a mental habit of bundling our life experience into five year periods. He believes at ages ending in five and zeros, we become self-reflective and take mental stock of our previous choices and our future options.

Many people sell their businesses after five years. The next major point of exit often comes at ten years. Anecdotally, Dinesh has noticed that, for example, milestones like founding companies, selling companies, bringing in investors, and raising money are notably tied to a five or zero number. Dinesh’s personal favorite is the “20 year overnight success.”

But staying the course is a process you can fully anticipate and plan for. As he explains:

It’s going to take longer than you think. So if you think it’s going to take three years, it’s probably going to take five years. If you think it’s going to take five years, then it’s probably going to take seven years. So if you commit to five, it’ll either force you to scale your idea to something you can execute in five and if you aren’t able to execute in five, you still have knowledge that you can go, “Look. That was that five years. I’m going to move on to the next five years and do either something different or do something that’s a variation.”

Expect to reflect

As Jason Treu observes, all businesses plateau. It’s only a matter of time until things slow down and you have to simply persist in applying yourself to your current vision and goals or reassess and try something different. Staying the course could then mean, “staying the course of your entrepreneurial journey” versus staying the course of a particular tactic, strategy, or even business line.

Some of my personal coping strategies during these uneventful and trying times is to look for ways to disengage from my expectations and enjoy the journey. Celebrating milestones is one example. Another is to simply focus on something else, whether that’s a hobby or other activity that refreshes me and renews my energy.

Reading business books and listening to podcasts can also be very helpful and supportive. I have found an uplifting sense of community and solidarity with other entrepreneurs by simply reading or listening to their stories. Between the experiences of some and the insights of others, I can’t help but be inspired and fortified to carry on.

Guy running down road with sunrise
Joshua Sortino

Some final Nevers

The bottom line is: You’re the captain of the ship.

What to do next will still and always be your call to make, regardless of your circumstances or how many people you may surround yourself with; regardless of how high or low the stakes may be.

But never give up, because it’s never too late to succeed.

All photos sourced from