Is that Bridge Safe? How to Cross the Gap Between Your Day Job and Make a Good Living at Self-Employment

by | Sep 5, 2011

I don’t know about you, but I’m afraid of heights. And the idea of walking across a rope bridge suspended high above the water gives me the heebie jeebies.

But sometimes a rope bridge is what you have to work with. In this article I’ll look at how you can construct and cross a stable rope bridge between your day job and full time self-employment—and make a good living at it.

The topic came up when a reader wrote: “I still have a four-day-a-week job, and moving into the next phase is proving very challenging, both practically and emotionally.” I know that’s a situation many people find themselves in. And in this economy it can be more important than ever to secure a self-employment income when jobs are uncertain. Here’s how to lay the groundwork so you can make a good living.

Assess the Gap

One of the bigger challenges in assessing the gap is reality testing. It’s easy to get revved up with enthusiasm and imagine the future is closer or easier to attain than it is. It’s equally easy to be assailed by doubts and see it further away or harder to reach than it is.

And then there is that unlovely way we can veer from one extreme to the other, never quite landing at the mid point of dispassionate assessment. (Ah, don’t you just love being human?)

Find the Right Questions

When it comes to assessing the gap (or any other part of crossing the bridge, for that matter) finding the right questions is key. Here are some questions I would ask you if we were having a coaching conversation.

1. What’s on the other side of the gap?

What does full time self-employment look like? What kind of work will you be doing? For what kind of clients or customers? How do you imagine your ideal day or week?

What does it mean to make a good living? How much money for how much effort doing what kinds of things?

Spend some time here. Let yourself build as vivid and specific a picture as you can. Really feel into it. You can’t go there if you don’t know what there is. (!)

2. Why is having that important?

Why is it important that you be self-employed? What’s at stake?

What will you be able to be, do, or have as a result? And why is that important?

Keep asking “Why is that important?” with each successive answer until you reach bedrock. Until you recognize a fundamental, compelling reason for going for it.

Because you’re going to need that where you’re going.

3. Where are you now?

What’s your current situation? What do you like or dislike about your current work (or lack of it)? How are you living in or out of alignment with your core values? What are you doing or not doing to maintain a healthy, happy lifestyle?

4. What needs to happen for you to cross the gap?

What steps do you envision between where you are now and where you want to be?
Depending on your cognitive style, you might come at this question in different ways. You could imagine that you are fully self-employed, then walk backward. Think about the steps in reverse order. What’s the last thing that happened before you were fully across? And what came before that?

You could also brainstorm using post-its or a mind map to capture steps in no particular order. When you’ve got them down, play with them, grouping them in whatever way makes sense. This is a good way to integrate right and left brain thinking.

And if you’re a linear visionary, go ahead and outline the steps beginning where you are now and working forward.

A caveat: Whatever method you use, don’t get too hung up on completeness. You can always backfill. In fact, you’ll want to deliberately revisit your steps frequently through the process of crossing the gap.

5. What’s the condition of the bridge?

You know what it looks like on either side of the gap, now picture what part of the bridge is in place and what parts need to be built or reinforced.

I don’t know about you, but this is where I tend to freeze or brazen my way across, neither of which is particularly constructive. (And now you know my default mode. I’m telling you, if I can do this, you can do this.)

The best way to assess the condition of your bridge is to check with others who have crossed the gap. Ask where they were when they started out and what they had to do to get across. What surprises did they run into? What do they wish they had known in advance? What would have made it easier for them to make a good living?

No two people have an identical bridge, so ask several people at this stage.

6. What’s your tolerance for risk?

There’s no right or wrong answer here, but it is essential that you ask this question. You have to know what kind of safety net you need in order to cross with confidence. A certain amount of anxiety goes with the territory, but only you know where anxiety shades over into debilitating fear.

I see people all the time get hung up because they don’t ask and answer this question. Because they don’t know their own risk tolerance, they take smaller or bigger risks than they should. When they risk too little, the flame of peaceful ambition can flicker and die. When they risk to much, they can crash and burn.

Make a Plan

When you’ve asked and answered these questions, you know a lot about yourself and the gap you want to bridge. What remains is to make a plan and put it in action.

Start with your safety net. If you need to save money or cash in investments to bridge the gap between your current job and full time self-employment, get that in order first. Also, gather your emotional support system. Don’t expect to make a good living right away.

Create a calendar. Decide on a date when you will be fully self-employed. Use your answers to question 4, above, to fill in dates by when you will have taken each step.
Budget for just-in-time learning. As you plan and take action, you’re going to discover all sorts of things you need to learn. Expect to invest time, energy, and money in learning at each step of the way.

(Speaking of learning, consider the support of Profit Alchemy. In nine months you’ll be shown step-by-step how to cross the gap.)

What if You Get Stuck?

It happens. You get out on the bridge and suddenly you freeze. Perhaps there’s an unexpected obstacle or unanticipated challenge. Maybe you’re way more scared than you expected to be.

Here’s where a support system makes all the difference. Friends. Family. Peers. Coaches. Nobody does this alone. I’ve been self-employed since 1989, and I wouldn’t dream of going it alone. In fact, the longer I work for myself, the more I rely on support so I can continue to make a good living.

(And if you think that’s a pitch for coaching or for one of my programs, I guess it is. I’d rather ruffle a few feathers than see one more person hang back or fail for lack of help.)

Like I Said, You Can Do This

I meant it when I said, if I can do make a good living, you can. I believe that. I wasn’t born a business woman. To this day I struggle with demons inside and out. That’s why I call self-employment a path of personal transformation.And if you’re up for that, you can do this.

Profit Alchemy: Like Magic but Real

Profit Alchemy is an integrated, intensive, transformative nine-month program that shows you step-by-step how to cross the bridge and make a profit at self-employment. The early application deadline for 2013 is Friday, December 21, 2012. Click here to learn more about Profit Alchemy.