How do you know it's time to go it alone?

A few weeks ago, a friend of mine asked: “how do you know when it’s time to go it alone?”

I’ve now been self-employed for 6 months (for the second time, after starting, growing and selling Rise at Seven) and I think there are 7 boxes you’ll want to tick (most of):

1. You *want* to be self-employed

Firstly, you like the idea of being your own boss (and don’t mind doing the things a boss does). You think the admin is totally worth it. You quite like meeting new people, actually, and the sales thing doesn’t scare you too much.

If you feel like you’re being peer pressured into this by LinkedIn, turn back now (note: being peer pressured into this by someone who genuinely cares about you and wants the best for you is different).

There are lots of reasons why self-employment makes economic sense, but economic sense is not the only thing that matters. Employment gives you a consistent wage (is that super important to you?) and a social environment (do you have one elsewhere?)

2. You know what you want to do and who you want to do it for

This will probably be hypothetical, but if you have absolutely no idea what services you will offer, or who will buy these services from you, then you need to do some research before you go any further.

I’ve always found Jim Collins’ Hedgehog Concept is a good way to think about this.

• You need to be passionate about the service because there will be no osmosis in the office (for the time being) - your learning will be self-directed and hands-on, so you’ve got to want to do it
• You need it to be something people will pay for
• You need to be good at it because there are a lot of alternatives your clients could use (not just other freelancers: they could appoint an agency; use ChatGPT; learn it themselves; hire someone internally; completely ignore the problem and hope it goes away). You don’t need to be the best in the world (I do, but that’s my problem, not yours) but you do need to be the best in their world (e.g. they know about you and are more willing to work with you than they are to work with others)

Which leads us onto…

3. You know where your work will come from

Your self-employed life will be much easier if you do some of the hard work before you start (ideally while someone else is paying for it, because they benefit too). One or two of these will be a good start:

• You have a founding client or two
• You have a social following (of professionals, who might buy things)
• You have a database (like a mailing list)
• You have at least a few former clients who you have spoken to and know want to work with you again
• You have strong sales skills and you believe in your own track record

Investing your time into these things benefits your current employer, there’s nothing disingenuous about it. The week we launched Rise at Seven, we got 16 leads and 23 job applications from about 450,000 social media impressions…this was possible because I already had 20,000 social followers (and our lead generation only accelerated as my co-founder, Carrie Rose, rapidly gained more followers and soon eclipsed my public profile).

4. You’ve saved 3 (ideally 6) months of bills and expenses

I didn’t bill anything in April 2025, my first month. It takes time to set up calls and close deals, plus it’s common to be paid in arrears (which I am, for about a third of the work I do now…and in some disciplines it’ll be even more common). You don’t want to have to close something to put food on the table and you don’t want to have to compromise to save your house. I don’t think clients can smell fear, but they can smell desperation, and if you’re in a weak negotiating position you’re going to make things much harder for yourself.

I would like to be able to make this statement to my significant other: “we have enough saved up that I could take the next 6 months off completely and we’d be fine.”

5. You know an accountant

You’ve got enough cash to pay an accountant to help you set the business up. Perhaps you want the aforementioned significant other to be a co-director in your new Ltd company and someone needs to help you make that happen. Assuming you work in professional services, you probably want to be VAT registered. You’ll probably need some “making tax digital” software like Xero or QuickBooks - an accountant will be able to set this up for you.

It’s entirely feasible that you can start to cost yourself money before you’ve even started and even an average accountant will help you to make sure this doesn’t happen.

You’ll need a lawyer far less often than you think you might and you’ll need an accountant far more frequently than you can imagine.

If you don't know a good one, ask me or people you know for some recommendations.

6. You know who will cheer for you

Lastly, but not to be overlooked, there are people around you (ideally other professionals, with friends they can refer to you - but loved ones will do) who will keep you positive and ask you about your day. The self-employed life is a lonely one, whether you’re a sole trader or a founder with a couple of hundred employees. Once you have enough cash, get a mentor or non-executive director, or find someone who will play that role for you for free, if you can. Be in a WhatsApp group or two. Go to some networking events. Meet up with some other self-employed types once or twice a month. There will come a time when you might miss the ping of a Slack notification (to be absolutely clear - I personally do not miss that).

7. You understand you will be tested every day

Until you go self-employed, the thought will cross your mind on occasion: "what if?"

What if I was my own boss...how good would life be?

You have to understand that when you've made the leap, you'll catch yourself thinking the opposite.

What if I had a steady wage and a full time job and colleagues and I didn't have to worry about this and that?

Even I think like that sometimes. It's not going to go away. Here's what I'd ultimately suggest:

If you think about an alternate future where you're self-employed more than you think about the likely future you have in your current job, then you've probably made the decision already.

Ultimately...

I don't buy into the sentiment that "if it's easy, everyone would do it."

After exiting my agency and taking 18 months off to be a stay-at-home dad, I went back into full time employment because it was what I felt I needed at the time. I needed some consistency and, especially, a place to go to get out of the house, filled with grown ups to talk to about something I'm passionate about.

I'm glad I did because it has meant that I am now absolutely clear that I'm doing what I should be doing as a management consultant for marketing agencies.