Success Isn't About Making One Big Decision, It's About Making a Million Small Decisions Finding success in entrepreneurship is a constant balancing act between decision-making, risk management and leadership.

By Scott Wylie

Opinions expressed by Entrepreneur contributors are their own.

I was lucky. I saw it coming.

Early in my career I started a bank in San Juan, Puerto Rico. I was in a good place professionally and I liked everything about my role—the business climate was great, the community was supportive, and the weather was exceptional.

There was just one problem: my wife didn't want to spend our entire lives in the Caribbean.

So we did what any good partners do and made a deal. We would only stay for five years, and then when our time was up we would move back to Denver and I would hand off my CEO role in the company I had started. It wasn't how I expected that part of my career to unfold, but because of our agreement the decision was already predetermined.

The end was knowable. Which is usually not true for most entrepreneurs.

Choices aren't always obvious

It's often assumed that the major pivot points for business owners arrive alongside a blare of sirens and blinding lights. The choice is obvious and the choice is always binary: for example, you can either sell the company you've built and cash out or double down and work harder to make it grow to achieve success.

Except it's never that simple.

Related: 8 Success Lessons From the Richest Person on the Planet

In my experience, these two clear-cut paths are more like a mirage. Instead, grow versus sell are merely two ends on a long continuum, a spectrum every entrepreneur sits on at every moment of their career whether they realize it or not.

The pivot point may eventually arrive, sure. But it typically won't do so on your schedule, and no entrepreneur can truly be prepared for it unless they're constantly assessing where they live on that spectrum.

This assessment can be especially tricky for the person who is by design meant to lead with unblinking authority. Projecting the utmost confidence in the direction you're headed is not possible if you're also publicly asking people if they think you're headed down the right path. Do that with your employees and they might just start looking for a new job. Do that with your investors and they might just find someone new to grow their money.

So what's a good entrepreneur to do?

No one succeeds alone

Given the rapid-fire nature of the business world, whether or not you're in a place to grow or sell needs to be part of a conversation you're having with your own trusted network of mentors all the time. It's not that entrepreneurs aren't thoughtful about their own self interest, because they are. It's that they often view the problems they face in isolation, rather than as one piece of a very large, interconnected puzzle.

This is what I learned in the time it took me to go from starting my first bank to leading my fourth. If you're not in the process of recalibrating or figuring out where you stand going into the next challenge, there's a good chance that one of those other, previously invisible problems is going to push you towards making a decision whether you like it or not.

Related: Success Is Not an Entitlement, You Have to Earn It Every Day

I found myself in this exact position coming out of the Great Recession.

In that case, I had started a new bank which had been structured to survive a downturn. It was a move that proved prescient as we watched a lot of smaller banks fall by the wayside, undone by new regulations, higher capital requirements, and the loan losses that hit the industry during any recession.

But that pivot point came with new questions. Should we hunker down and just hope to survive or go into growth mode and expand as others exited? Were we growing or selling?

We spent a lot of time talking with our stakeholders – the management team, the board, our shareholders, our associates, our clients, and more – to determine if we were on the right path. Ultimately we decided the best path for shareholder value creation was taking our company public and in the process aggressively expanding our mission as an organization.

But the key for me, at least, was that I had already had many of these same conversations with members of my trusted network well before I ever spoke to stakeholders. The intervening years between the easy decision in Puerto Rico and the worst economic period since the Great Depression had taught me many lessons, but chief among them was that if I wasn't constantly reassessing my position and the position of the company I was running, some external factor would catch me unprepared.

Related: 7 Mindsets That Guarantee Enduring Success

I knew what I wanted from the bank well before forces beyond my control pushed me towards that pivot point. And I had been fortunate enough to build a network of advisors I could turn to who understood the challenges entrepreneurs face but weren't connected to the outcomes of my decisions.

Success isn't a one-person endeavor

This is a variation of a concept I've talked about in the past: watching your backside. That is, the part of an entrepreneur's personal life they don't show to the wider world, but only to a trusted few, whether they be family members, mentors, or anyone else with a stake in their success but no clear stake in the success of their business.

The truth is, entrepreneurship is a constant balancing act of decision-making, risk management, and leadership. And the roadmap for founders isn't much of a map at all.

Those that succeed are those that embrace this uncertainty and work to balance the wants and needs of all stakeholders involved – including themselves – well before the inevitable pivot point comes calling. Those that overlook these preparations might find themselves making tough decisions before they're ready, and possibly regretting them later.

Wavy Line
Scott Wylie

Chairman and CEO, First Western

Scott Wylie co-founded First Western in 2002 after recognizing the need for an integrated approach for delivering financial services to the growing affluent market. As chairman and CEO of First Western, Wylie provides leadership for the holding company, as well as management of the bank and trust services. Most recently, he served as chairman and CEO of Northern Trust Bank of Colorado after having sold his prior institution, Trust Bank of Colorado, to Northern in 1998.

Editor's Pick

A Father Decided to Change When He Was in Prison on His Son's Birthday. Now His Nonprofit Helps Formerly Incarcerated Applicants Land 6-Figure Jobs.
A Teen Turned His Roblox Side Hustle Into a Multimillion-Dollar Company — Now He's Working With Karlie Kloss and Elton John
3 Mundane Tasks You Should Automate to Save Your Brain for the Big Stuff
The Next Time Someone Intimidates You, Here's What You Should Do
5 Ways to Manage Your Mental Health and Regulate Your Nervous System for Sustainable Success

Related Topics

Business News

'Do You Hate Me?': High School Teacher Shares Wild Emails He Receives From Students

Jordan Baechler teaches high school students in Ontario, Canada.

Business News

Hedge Fund Pays NYC Interns $20,000 a Month on Average, Sent to Lavish Palm Beach Kickoff

Citadel is known for its over-the-top parties and company retreats.

Data & Recovery

This Father's Day, Give the Gift of No More Low Storage Warnings

Save 85% on 1TB of cloud storage for Father's Day.

Growing a Business

Do You Say 'Like' Too Much? Don't Worry! I'm a Sociolinguist, and I Like 'Like.'

The modern use of the word is denigrated through and through. But it may be doing more communicative heavy lifting than we give it credit for.

Starting a Business

Starting a New Business? Here's How to Leverage Transferable Skills From Your Prior Careers and Drive Success

Launching your own business can be daunting, but when you harness the skills from past jobs, there are a variety of things you must ask yourself. Here are three recipes for success using your prior experiences.